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<span>Scope</span> </div> </a> <ul id="toc-Scope-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Variations" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Variations"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Variations</span> </div> </a> <ul id="toc-Variations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Asymmetric_Stetter_Reaction" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Asymmetric_Stetter_Reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Asymmetric Stetter Reaction</span> </div> </a> <ul id="toc-Asymmetric_Stetter_Reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span 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data-mw-deduplicate="TemplateStyles:r1049416944">.mw-parser-output .ib-reactionbox{border-collapse:collapse}.mw-parser-output .ib-reactionbox td,.mw-parser-output .ib-reactionbox th{border:1px solid #a2a9b1}</style> <table class="infobox ib-reactionbox"> <tbody><tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Stetter reaction </th></tr> <tr> <td>Named after </td> <td>Hermann Stetter </td></tr> <tr> <td>Reaction type </td> <td><a href="/wiki/Coupling_reaction" title="Coupling reaction">Coupling reaction</a> </td></tr> <tr> <th style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2">Identifiers </th></tr> <tr> <td>Organic Chemistry Portal </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/stetter-reaction.shtm">stetter-reaction</a></span> </td></tr> <tr> <td style="width: 30%; background: #ACE1AF; text-align: center;" colspan="2"> </td></tr> </tbody></table> <p>The <b>Stetter reaction</b> is a reaction used in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> to form <a href="/wiki/Carbon-carbon_bond" class="mw-redirect" title="Carbon-carbon bond">carbon-carbon bonds</a> through a <a href="/wiki/1,4-addition" class="mw-redirect" title="1,4-addition">1,4-addition</a> reaction utilizing a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-Stetter_1-0" class="reference"><a href="#cite_note-Stetter-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> While the related <a href="/wiki/1,2-addition" class="mw-redirect" title="1,2-addition">1,2-addition</a> reaction, the <a href="/wiki/Benzoin_condensation" title="Benzoin condensation">benzoin condensation</a>, was known since the 1830s, the Stetter reaction was not reported until 1973 by Dr. Hermann Stetter.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The reaction provides synthetically useful 1,4-dicarbonyl compounds and related derivatives from aldehydes and <a href="/wiki/Michael_acceptor" class="mw-redirect" title="Michael acceptor">Michael acceptors</a>. Unlike 1,3-dicarbonyls, which are easily accessed through the <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a>, or 1,5-dicarbonyls, which are commonly made using a <a href="/wiki/Michael_reaction" class="mw-redirect" title="Michael reaction">Michael reaction</a>, 1,4-dicarbonyls are challenging substrates to synthesize, yet are valuable starting materials for several organic transformations, including the <a href="/wiki/Paal%E2%80%93Knorr_synthesis" title="Paal–Knorr synthesis">Paal–Knorr synthesis</a> of <a href="/wiki/Furan" title="Furan">furans</a> and pyrroles. Traditionally utilized catalysts for the Stetter reaction are thiazolium salts and cyanide anion, but more recent work toward the asymmetric Stetter reaction has found triazolium salts to be effective. The Stetter reaction is an example of <a href="/wiki/Umpolung" title="Umpolung">umpolung</a> chemistry, as the inherent polarity of the aldehyde is reversed by the addition of the catalyst to the aldehyde, rendering the carbon center nucleophilic rather than electrophilic. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stetter_reaction_general_example.png" class="mw-file-description" title="Scheme 1. Stetter reaction overview"><img alt="Scheme 1. Stetter reaction overview" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Stetter_reaction_general_example.png/400px-Stetter_reaction_general_example.png" decoding="async" width="400" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Stetter_reaction_general_example.png/600px-Stetter_reaction_general_example.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Stetter_reaction_general_example.png/800px-Stetter_reaction_general_example.png 2x" data-file-width="1287" data-file-height="284" /></a><figcaption>Scheme 1. Stetter reaction overview</figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Mechanism">Mechanism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=1" title="Edit section: Mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As the Stetter reaction is an example of <a href="/wiki/Umpolung" title="Umpolung">umpolung</a> chemistry, the aldehyde is converted from an <a href="/wiki/Electrophile" title="Electrophile">electrophile</a> to a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> under the reaction conditions.<sup id="cite_ref-Tetreview_3-0" class="reference"><a href="#cite_note-Tetreview-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This is accomplished by activation from some catalyst - either cyanide (CN<sup>−</sup>) or thiazolium salt.<sup id="cite_ref-Stetter_1-1" class="reference"><a href="#cite_note-Stetter-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> For the use of either catalyst, the mechanism is very similar; the only difference is that with thiazolium salts, the catalyst must be deprotonated first to form the active catalytic species. The active catalyst can be described as the combination of two contributing <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> forms - an <a href="/wiki/Ylide" title="Ylide">ylide</a> or a <a href="/wiki/Carbene" title="Carbene">carbene</a>, both of which portray the nucleophilic character at carbon. The thiazolium ylide or CN<sup>−</sup> can then add into the aldehyde substrate, forming a cyanohydrin in the case of CN<sup>−</sup> or the Breslow intermediate in the case of thiazolium salt. The Breslow intermediate was proposed by <a href="/wiki/Ronald_Breslow" title="Ronald Breslow">Ronald Breslow</a> in 1958 and is a common intermediate for all <a href="/wiki/Thiamine" title="Thiamine">thiamine</a>-catalyzed reactions, whether <i>in vitro</i> or <i>in vivo</i>.<sup id="cite_ref-Breslow_4-0" class="reference"><a href="#cite_note-Breslow-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Breslow_intermediate_formation.png" class="mw-file-description" title="Scheme 2. Formation of the Breslow intermediate"><img alt="Scheme 2. Formation of the Breslow intermediate" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Breslow_intermediate_formation.png/500px-Breslow_intermediate_formation.png" decoding="async" width="500" height="241" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Breslow_intermediate_formation.png/750px-Breslow_intermediate_formation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Breslow_intermediate_formation.png/1000px-Breslow_intermediate_formation.png 2x" data-file-width="1687" data-file-height="812" /></a><figcaption>Scheme 2. Formation of the Breslow intermediate</figcaption></figure> <p>Once the "nucleophilic aldehyde" <a href="/wiki/Synthon" title="Synthon">synthon</a> is formed, whether as a cyanohydrin or stabilized by a thiazolium ylide, the reaction can proceed down two pathways. The faster pathway is self-condensation with another molecule of aldehyde to give benzoin products. However, <a href="/wiki/Benzoin_condensation" title="Benzoin condensation">benzoin condensation</a> is completely reversible, and therefore does not interfere with product formation in the Stetter reaction. In fact, benzoins can be used instead of aldehydes as substrates to achieve the same overall Stetter transformation, because benzoins can be restored to their aldehyde precursors under the reaction conditions.<sup id="cite_ref-Stetter_1-2" class="reference"><a href="#cite_note-Stetter-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The desired pathway toward the Stetter product is the 1,4-addition of the nucleophilic aldehyde to a Michael-type acceptor. After 1,4-addition, the reaction is irreversible and ultimately, the 1,4-dicarbonyl is formed when the catalyst is kicked out to regenerate CN<sup>−</sup> or the thiazolium ylide. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stetter_reaction_mechanism.png" class="mw-file-description" title="Scheme 3. Mechanism of the Stetter reaction"><img alt="Scheme 3. Mechanism of the Stetter reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Stetter_reaction_mechanism.png/500px-Stetter_reaction_mechanism.png" decoding="async" width="500" height="397" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Stetter_reaction_mechanism.png/750px-Stetter_reaction_mechanism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/Stetter_reaction_mechanism.png/1000px-Stetter_reaction_mechanism.png 2x" data-file-width="1780" data-file-height="1414" /></a><figcaption>Scheme 3. Mechanism of the Stetter reaction</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Scope">Scope</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=2" title="Edit section: Scope"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Stetter reaction produces classically difficult to access 1,4-dicarbonyl compounds and related derivatives. The traditional Stetter reaction is quite versatile, working on a wide variety of substrates.<sup id="cite_ref-Stetter_1-3" class="reference"><a href="#cite_note-Stetter-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Aromatic aldehydes, heteroaromatic aldehydes, and benzoins can all be used as acyl anion precursors with thiazolium salt and cyanide catalysts. However, aliphatic aldehydes can only be utilized if a thiazolium salt is used as a catalyst, as they undergo aldol condensation side reaction when a cyanide catalyst is used. In addition, α,β-unsaturated esters, ketones, nitriles, nitros, and aldehydes are all appropriate Michael acceptors with either catalyst. However, the general scope of <a href="#Asymmetric_Stetter_Reaction">asymmetric Stetter reactions</a> is more limited. Intramolecular asymmetric Stetter reactions enjoy a range of acceptable Michael acceptors and acyl anion precursors in essentially any combination.<sup id="cite_ref-JOCscope_5-0" class="reference"><a href="#cite_note-JOCscope-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Intramolecular asymmetric Stetter reactions can utilize aromatic, heteroaromatic and aliphatic aldehydes with a tethered α,β-unsaturated ester, ketone, thioester, malonate, nitrile or Weinreb amide. It has been shown that α,β-unsaturated nitros and aldehydes are not suitable Michael acceptors and have markedly decreased enantiomeric excess in such reactions.<sup id="cite_ref-JOCscope_5-1" class="reference"><a href="#cite_note-JOCscope-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Another limitation encountered with intramolecular asymmetric Stetter reactions is that only substrates that result in the formation of a six-membered ring show synthetically useful enantiomeric excess; substrates which form five and seven-membered rings either do not react or show low stereoinduction.<sup id="cite_ref-JOCscope_5-2" class="reference"><a href="#cite_note-JOCscope-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> On the other hand, intermolecular asymmetric reactions are quite confined to specifically matched combinations of acyl anion precursor and Michael acceptor, such as an aliphatic aldehyde with a nitroalkene.<sup id="cite_ref-Glorius_6-0" class="reference"><a href="#cite_note-Glorius-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In addition, these substrates tend to be rather activated, as the intermolecular asymmetric Stetter reaction is still in the early stages of development. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Scope_of_Stetter_Reaction.png" class="mw-file-description" title="Scheme 4. Scope of Stetter Reaction"><img alt="Scheme 4. Scope of Stetter Reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Scope_of_Stetter_Reaction.png/600px-Scope_of_Stetter_Reaction.png" decoding="async" width="600" height="410" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Scope_of_Stetter_Reaction.png/900px-Scope_of_Stetter_Reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Scope_of_Stetter_Reaction.png/1200px-Scope_of_Stetter_Reaction.png 2x" data-file-width="2002" data-file-height="1367" /></a><figcaption>Scheme 4. Scope of Stetter Reaction</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Variations">Variations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=3" title="Edit section: Variations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several variations of the Stetter reaction have been developed since its discovery in 1973. In 2001, Murry <i>et al</i> reported a Stetter reaction of aromatic aldehydes onto acylimine derivatives to give α-amido ketone products.<sup id="cite_ref-acylimines_7-0" class="reference"><a href="#cite_note-acylimines-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The acylimine acceptors were generated <i>in situ</i> from α-tosylamide substrates, which underwent elimination in the presence of base. Good to excellent yields (75-90%) were observed. Mechanistic investigations showed that the corresponding benzoins were not adequate substrates, contrary to traditional Stetter reactions.<sup id="cite_ref-Stetter_1-4" class="reference"><a href="#cite_note-Stetter-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> From this, the authors conclude the Stetter reaction of acylimines is under kinetic control, rather than thermodynamic control. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stetter_reaction_with_acylimines.png" class="mw-file-description" title="Scheme 5. Stetter reaction with acylimines as acceptors"><img alt="Scheme 5. Stetter reaction with acylimines as acceptors" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Stetter_reaction_with_acylimines.png/500px-Stetter_reaction_with_acylimines.png" decoding="async" width="500" height="219" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Stetter_reaction_with_acylimines.png/750px-Stetter_reaction_with_acylimines.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Stetter_reaction_with_acylimines.png/1000px-Stetter_reaction_with_acylimines.png 2x" data-file-width="1677" data-file-height="736" /></a><figcaption>Scheme 5. Stetter reaction with acylimines as acceptors</figcaption></figure> <p>Another variation of the Stetter reaction involves the use of 1,2-dicarbonyls as precursors to the acyl anion intermediate. In 2005, Scheidt and coworkers reported the use of sodium pyruvate, which loses CO<sub>2</sub> to form the Breslow intermediate.<sup id="cite_ref-decarboxylative_8-0" class="reference"><a href="#cite_note-decarboxylative-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Similarly, in 2011 Bortolini and coworkers demonstrated the use of α-diketones to generate an acyl anion.<sup id="cite_ref-diketones_9-0" class="reference"><a href="#cite_note-diketones-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Under the conditions they developed, 2,3-butadienone is cleaved after addition to the thiazolium catalyst to release ethyl acetate and generate the Breslow intermediate necessary for the Stetter reaction to proceed. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Stetter_reaction_with_acyclic_diketones.png" class="mw-file-description" title="Scheme 6. Stetter reaction with acyclic α-diketones"><img alt="Scheme 6. Stetter reaction with acyclic α-diketones" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Stetter_reaction_with_acyclic_diketones.png/500px-Stetter_reaction_with_acyclic_diketones.png" decoding="async" width="500" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Stetter_reaction_with_acyclic_diketones.png/750px-Stetter_reaction_with_acyclic_diketones.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Stetter_reaction_with_acyclic_diketones.png/1000px-Stetter_reaction_with_acyclic_diketones.png 2x" data-file-width="1755" data-file-height="918" /></a><figcaption>Scheme 6. Stetter reaction with acyclic α-diketones</figcaption></figure> <p>In addition, they showed the atom economy and utility of using a cyclic α-diketone to generate the Stetter product with a tethered ethyl ester. The reaction precedes through the same mechanism as the acyclic version, but the ester generated by attack of ethanol remains tethered to the product. However, the conditions only allow for the generation of ethyl esters, due to the necessity of ethanol as solvent. Substitution of ethanol with <i>tert</i>-butanol resulted in no product. The authors speculate this is due to the difference in acidity between the two alcoholic solvents. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Reaction_scheme_of_cyclic_diketone_stetter_reaction.png" class="mw-file-description" title="Scheme 7. Stetter reaction with cyclic α-diketones"><img alt="Scheme 7. Stetter reaction with cyclic α-diketones" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Reaction_scheme_of_cyclic_diketone_stetter_reaction.png/500px-Reaction_scheme_of_cyclic_diketone_stetter_reaction.png" decoding="async" width="500" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Reaction_scheme_of_cyclic_diketone_stetter_reaction.png/750px-Reaction_scheme_of_cyclic_diketone_stetter_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Reaction_scheme_of_cyclic_diketone_stetter_reaction.png/1000px-Reaction_scheme_of_cyclic_diketone_stetter_reaction.png 2x" data-file-width="1576" data-file-height="419" /></a><figcaption>Scheme 7. Stetter reaction with cyclic α-diketones</figcaption></figure> <p>In 2004, Scheidt and coworkers introduced acyl silanes as competent substrates in the Stetter reaction, a variation they termed the "sila-Stetter reaction."<sup id="cite_ref-silastetter2004_10-0" class="reference"><a href="#cite_note-silastetter2004-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Under their reaction conditions, the thiazolium catalyst induces a [1,2] <a href="/wiki/Brook_rearrangement" title="Brook rearrangement">Brook rearrangement</a>, which is followed by desilylation by an isopropanol additive to give the common Breslow intermediate of the traditional Stetter reaction. The desilylation step was found to be necessary, and the reaction does not proceed without an alcoholic additive. Acyl silanes are less electrophilic than the corresponding aldehydes, preventing typical benzoin-type byproducts often observed in the Stetter reaction.<sup id="cite_ref-silastetter2006_11-0" class="reference"><a href="#cite_note-silastetter2006-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Silastetter_Reaction.png" class="mw-file-description" title="Scheme 8. Sila-Stetter reaction"><img alt="Scheme 8. Sila-Stetter reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Silastetter_Reaction.png/600px-Silastetter_Reaction.png" decoding="async" width="600" height="270" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Silastetter_Reaction.png/900px-Silastetter_Reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Silastetter_Reaction.png/1200px-Silastetter_Reaction.png 2x" data-file-width="2122" data-file-height="954" /></a><figcaption>Scheme 8. Sila-Stetter reaction</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Asymmetric_Stetter_Reaction">Asymmetric Stetter Reaction</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=4" title="Edit section: Asymmetric Stetter Reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first <a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">asymmetric</a> variant of the Stetter reaction was reported in 1996 by Enders <i>et al</i>, employing a chiral triazolium catalyst <b>1</b>.<sup id="cite_ref-Enders_12-0" class="reference"><a href="#cite_note-Enders-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Subsequently, several other catalysts were reported for asymmetric Stetter reactions, including <b>2</b>,<sup id="cite_ref-Rovis2002_13-0" class="reference"><a href="#cite_note-Rovis2002-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <b>3</b>,<sup id="cite_ref-Bach2004_14-0" class="reference"><a href="#cite_note-Bach2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and <b>4</b>.<sup id="cite_ref-Miller2005_15-0" class="reference"><a href="#cite_note-Miller2005-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:First_Asymmetric_Stetter_Reactions.png" class="mw-file-description" title="Scheme 9. First Asymmetric Stetter Reactions"><img alt="Scheme 9. First Asymmetric Stetter Reactions" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/First_Asymmetric_Stetter_Reactions.png/600px-First_Asymmetric_Stetter_Reactions.png" decoding="async" width="600" height="432" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/First_Asymmetric_Stetter_Reactions.png/900px-First_Asymmetric_Stetter_Reactions.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/First_Asymmetric_Stetter_Reactions.png/1200px-First_Asymmetric_Stetter_Reactions.png 2x" data-file-width="2058" data-file-height="1481" /></a><figcaption>Scheme 9. First Asymmetric Stetter Reactions</figcaption></figure> <p>The success of the Rovis group's catalyst <b>2</b> led them to further explore this family of catalysts and expand their use for asymmetric Stetter reactions. In 2004, they reported the enantioselective formation of <a href="/wiki/Carbon-carbon_bond" class="mw-redirect" title="Carbon-carbon bond">quaternary</a> centers from aromatic aldehydes in an intramolecular Stetter reaction with a slightly modified catalyst.<sup id="cite_ref-Rovisquatcenters2004_16-0" class="reference"><a href="#cite_note-Rovisquatcenters2004-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Further work extended the scope of this reaction to include aliphatic aldehydes as well.<sup id="cite_ref-RovisTet2006_17-0" class="reference"><a href="#cite_note-RovisTet2006-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Subsequently, it was shown that the olefin geometry of the Michael acceptor dictates <a href="/wiki/Diastereomer" title="Diastereomer">diastereoselectivity</a> in these reactions, whereby the catalyst dictates the enantioselectivity of the initial carbon bond formation and <a href="/wiki/Allylic_strain" title="Allylic strain">allylic strain</a> minimization dictates the diastereoselective intramolecular protonation.<sup id="cite_ref-Rovis2005_18-0" class="reference"><a href="#cite_note-Rovis2005-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Quaternary_Center_Formation.png" class="mw-file-description" title="Scheme 10. Formation of quaternary centers"><img alt="Scheme 10. Formation of quaternary centers" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Quaternary_Center_Formation.png/600px-Quaternary_Center_Formation.png" decoding="async" width="600" height="387" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Quaternary_Center_Formation.png/900px-Quaternary_Center_Formation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Quaternary_Center_Formation.png/1200px-Quaternary_Center_Formation.png 2x" data-file-width="2187" data-file-height="1409" /></a><figcaption>Scheme 10. Formation of quaternary centers</figcaption></figure> <p>The inherent difficulties of controlling enantioselectivity in intermolecular reactions made the development of an intermolecular asymmetric Stetter reaction a challenge. While limited enantiomeric excess had been reported by Enders in the early 1990s for the reaction of <i>n</i>-butanal with chalcone,<sup id="cite_ref-Endersinter1_19-0" class="reference"><a href="#cite_note-Endersinter1-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> conditions for a synthetically useful asymmetric intermolecular Stetter reaction were not reported until 2008 when both the groups of Enders and Rovis published such reactions. The Enders group utilized a triazolium-based catalyst to effect the coupling of aromatic aldehydes with chalcone derivatives with moderate yields.<sup id="cite_ref-Endersinter2_20-0" class="reference"><a href="#cite_note-Endersinter2-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The concurrent publication from the Rovis group also employed a triazolium-based catalyst and reported the Stetter reaction between glyoxamides and alkylidenemalonates in good to excellent yields.<sup id="cite_ref-Rovisglyoxamides_21-0" class="reference"><a href="#cite_note-Rovisglyoxamides-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Asymmetric_Intermolecular_Stetter_Reactions.png" class="mw-file-description" title="Scheme 12. First Asymmetric Intermolecular Stetter Reactions"><img alt="Scheme 12. First Asymmetric Intermolecular Stetter Reactions" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Asymmetric_Intermolecular_Stetter_Reactions.png/500px-Asymmetric_Intermolecular_Stetter_Reactions.png" decoding="async" width="500" height="251" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Asymmetric_Intermolecular_Stetter_Reactions.png/750px-Asymmetric_Intermolecular_Stetter_Reactions.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Asymmetric_Intermolecular_Stetter_Reactions.png/1000px-Asymmetric_Intermolecular_Stetter_Reactions.png 2x" data-file-width="1919" data-file-height="965" /></a><figcaption>Scheme 12. First Asymmetric Intermolecular Stetter Reactions</figcaption></figure> <p>Rovis and coworkers subsequently went on to explore the asymmetric intermolecular Stetter reaction of heterocyclic aldehydes and <a href="/wiki/Nitroalkene" title="Nitroalkene">nitroalkenes</a>.<sup id="cite_ref-Rovis2009_22-0" class="reference"><a href="#cite_note-Rovis2009-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> During optimization of this reaction, it was found that a catalyst with a fluorinated backbone greatly enhanced enantioselectivity in the reaction. It was proposed that the fluorinated backbone helps to lock the conformation of the catalyst in a way the increases enantioselectivity. Further computational studies on this system verified that the <a href="/wiki/Stereoelectronics" class="mw-redirect" title="Stereoelectronics">stereoelectronic</a> attraction between the developing partial negative charge on the nitroalkene in the transition state and the partial positive charge of the C-F dipole is responsible for the increase in enantiomeric excess observed with the use of the catalyst with backbone fluorination.<sup id="cite_ref-Rovisfluorinatedcomp_23-0" class="reference"><a href="#cite_note-Rovisfluorinatedcomp-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> While this is a marked advance in the area of intermolecular asymmetric Stetter reactions, the substrate scope is limited and the catalyst is optimized for the specific substrates being utilized. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Asymmetric_Stetter_Reaction_with_Nitroalkenes.png" class="mw-file-description" title="Scheme 13. Asymmetric Intermolecular Stetter Reaction with Nitroalkenes"><img alt="Scheme 13. Asymmetric Intermolecular Stetter Reaction with Nitroalkenes" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Asymmetric_Stetter_Reaction_with_Nitroalkenes.png/400px-Asymmetric_Stetter_Reaction_with_Nitroalkenes.png" decoding="async" width="400" height="291" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Asymmetric_Stetter_Reaction_with_Nitroalkenes.png/600px-Asymmetric_Stetter_Reaction_with_Nitroalkenes.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Asymmetric_Stetter_Reaction_with_Nitroalkenes.png/800px-Asymmetric_Stetter_Reaction_with_Nitroalkenes.png 2x" data-file-width="1389" data-file-height="1009" /></a><figcaption>Scheme 13. Asymmetric Intermolecular Stetter Reaction with Nitroalkenes</figcaption></figure> <p>Another contribution to the development of asymmetric intermolecular Stetter reactions came from Glorius and coworkers in 2011.<sup id="cite_ref-Glorius_6-1" class="reference"><a href="#cite_note-Glorius-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> They demonstrated the synthesis of α-amino acids enantioselectively by utilizing <i>N</i>-acylamido acrylate as the conjugate acceptor. Significantly, the reaction can be run on a 5 mmol scale without loss of yield or enantioselectivity. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Amino_acid_synthesis_with_Stetter_reaction.png" class="mw-file-description" title="Scheme 14. Enantioselective synthesis of amino acids with intermolecular Stetter reaction"><img alt="Scheme 14. Enantioselective synthesis of amino acids with intermolecular Stetter reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Amino_acid_synthesis_with_Stetter_reaction.png/500px-Amino_acid_synthesis_with_Stetter_reaction.png" decoding="async" width="500" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Amino_acid_synthesis_with_Stetter_reaction.png/750px-Amino_acid_synthesis_with_Stetter_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Amino_acid_synthesis_with_Stetter_reaction.png/1000px-Amino_acid_synthesis_with_Stetter_reaction.png 2x" data-file-width="1843" data-file-height="431" /></a><figcaption>Scheme 14. Enantioselective synthesis of amino acids with intermolecular Stetter reaction</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=5" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Stetter reaction is an effective tool in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. The products of the Stetter reaction, 1,4-dicarbonyls, are valuable moieties for the synthesis of complex molecules. For example, Trost and coworkers employed a Stetter reaction as one step in their synthesis of <i>rac</i>-hirsutic acid C.<sup id="cite_ref-Trost_24-0" class="reference"><a href="#cite_note-Trost-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The intramolecular coupling of an aliphatic aldehyde with a tethered α,β-unsaturated ester led to the desired tricyclic 1,4-dicarbonyl in 67% yield. This intermediate was converted into <i>rac</i>-hirsutic acid C in seven more steps. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Hirsutic_acid_c.png" class="mw-file-description" title="Scheme 15. Total synthesis of hirsutic acid c utilizing an intramolecular Stetter reaction"><img alt="Scheme 15. Total synthesis of hirsutic acid c utilizing an intramolecular Stetter reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Hirsutic_acid_c.png/600px-Hirsutic_acid_c.png" decoding="async" width="600" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Hirsutic_acid_c.png/900px-Hirsutic_acid_c.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Hirsutic_acid_c.png/1200px-Hirsutic_acid_c.png 2x" data-file-width="2089" data-file-height="391" /></a><figcaption>Scheme 15. Total synthesis of hirsutic acid c utilizing an intramolecular Stetter reaction</figcaption></figure> <p>The Stetter reaction is commonly used in sequence with the <a href="/wiki/Paal-Knorr_synthesis" class="mw-redirect" title="Paal-Knorr synthesis">Paal-Knorr synthesis</a> of furans and pyrroles, which a 1,4-dicarbonyl undergoes condensation with itself or in the presence of an amine under high temperature, acidic conditions. In 2001, Tius and coworkers reported the asymmetric total synthesis of roseophilin utilizing an intermolecular Stetter reaction to couple an aliphatic aldehyde with a cyclic enone.<sup id="cite_ref-roseophilin_25-0" class="reference"><a href="#cite_note-roseophilin-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> After <a href="/wiki/Ring-closing_metathesis" title="Ring-closing metathesis">ring-closing metathesis</a> and alkene reduction, the 1,4-dicarbonyl product was converted to a pyrrole via the Paal-Knorr synthesis and further elaborated to the natural product. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Roseophilin_synthesis.png" class="mw-file-description" title="Scheme 16. Total synthesis of roseophilin utilizing an intermolecular Stetter reaction and Paal-Knorr pyrrole synthesis"><img alt="Scheme 16. Total synthesis of roseophilin utilizing an intermolecular Stetter reaction and Paal-Knorr pyrrole synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Roseophilin_synthesis.png/600px-Roseophilin_synthesis.png" decoding="async" width="600" height="315" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Roseophilin_synthesis.png/900px-Roseophilin_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Roseophilin_synthesis.png/1200px-Roseophilin_synthesis.png 2x" data-file-width="2212" data-file-height="1163" /></a><figcaption>Scheme 16. Total synthesis of roseophilin utilizing an intermolecular Stetter reaction and Paal-Knorr pyrrole synthesis</figcaption></figure> <p>In 2004, a one-pot coupling-isomerization-Stetter-Paal Knorr sequence was reported.<sup id="cite_ref-one_pot_26-0" class="reference"><a href="#cite_note-one_pot-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> This procedure first utilizes palladium cross-coupling chemistry to couple aryl halides with propargylic alcohols to give α,β-unsaturated ketones, which can then undergo a Stetter reaction with an aldehyde. Once the 1,4-dicarbonyl compound is formed, heating in the presence of acid will give the furan, while heating in the presence of ammonium chloride and acid will give the pyrrole. The entire sequence is performed in one-pot with no work-up or purification between steps. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Coupling_Isomerization_Stetter_Paal_Knorr.png" class="mw-file-description" title="Scheme 17. One-pot coupling-isomerization-Stetter-Paal Knorr sequence"><img alt="Scheme 17. One-pot coupling-isomerization-Stetter-Paal Knorr sequence" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Coupling_Isomerization_Stetter_Paal_Knorr.png/500px-Coupling_Isomerization_Stetter_Paal_Knorr.png" decoding="async" width="500" height="338" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Coupling_Isomerization_Stetter_Paal_Knorr.png/750px-Coupling_Isomerization_Stetter_Paal_Knorr.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Coupling_Isomerization_Stetter_Paal_Knorr.png/1000px-Coupling_Isomerization_Stetter_Paal_Knorr.png 2x" data-file-width="1907" data-file-height="1290" /></a><figcaption>Scheme 17. One-pot coupling-isomerization-Stetter-Paal Knorr sequence</figcaption></figure> <p>Ma and coworkers developed an alternative method for accessing furans utilizing the Stetter reaction.<sup id="cite_ref-aminofuran1_27-0" class="reference"><a href="#cite_note-aminofuran1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In their report, 3-aminofurans are synthesized under Stetter conditions for coupling aromatic aldehydes with dimethyl acetylenedicarboxylate (DMAD), whereby the thiazolium ylide is hydrolyzed by the aromatization of the furan product. As the thiazolium is destroyed under these conditions, it is not catalytic and must be used in stoichiometric quantities. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:3-aminofurans_from_Stetter_chemistry.png" class="mw-file-description" title="Scheme 18. Synthesis of 3-aminofurans using Stetter chemistry"><img alt="Scheme 18. Synthesis of 3-aminofurans using Stetter chemistry" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/3-aminofurans_from_Stetter_chemistry.png/600px-3-aminofurans_from_Stetter_chemistry.png" decoding="async" width="600" height="246" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/3-aminofurans_from_Stetter_chemistry.png/900px-3-aminofurans_from_Stetter_chemistry.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/3-aminofurans_from_Stetter_chemistry.png/1200px-3-aminofurans_from_Stetter_chemistry.png 2x" data-file-width="2231" data-file-height="915" /></a><figcaption>Scheme 18. Synthesis of 3-aminofurans using Stetter chemistry</figcaption></figure> <p>They further elaborated on this work by developing a method in which 2-aminofurans are synthesized by cyclization onto a nitrile.<sup id="cite_ref-aminofuran2_28-0" class="reference"><a href="#cite_note-aminofuran2-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In this method, the thiazolium ylide is employed catalytically and the free amine product is generated. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:2-aminofurans_from_Stetter_chemistry.png" class="mw-file-description" title="Scheme 19. Synthesis of 2-aminofurans using Stetter chemistry"><img alt="Scheme 19. Synthesis of 2-aminofurans using Stetter chemistry" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/2-aminofurans_from_Stetter_chemistry.png/500px-2-aminofurans_from_Stetter_chemistry.png" decoding="async" width="500" height="255" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/2-aminofurans_from_Stetter_chemistry.png/750px-2-aminofurans_from_Stetter_chemistry.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/2-aminofurans_from_Stetter_chemistry.png/1000px-2-aminofurans_from_Stetter_chemistry.png 2x" data-file-width="1651" data-file-height="843" /></a><figcaption>Scheme 19. Synthesis of 2-aminofurans using Stetter chemistry</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Related">Related</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=6" title="Edit section: Related"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Baylis%E2%80%93Hillman_reaction" title="Baylis–Hillman reaction">Baylis–Hillman reaction</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Stetter_reaction&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Stetter-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Stetter_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Stetter_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Stetter_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Stetter_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Stetter_1-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text">Stetter, H. <i>Angew. 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J. <i>Synthesis</i> <b>2004</b>, <i>14</i>, 2391.</span> </li> <li id="cite_note-aminofuran1-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-aminofuran1_27-0">^</a></b></span> <span class="reference-text">Ma, C.; Yang, Y. <i>Org Lett.</i> <b>2005</b>, <i>7</i>,1343.</span> </li> <li id="cite_note-aminofuran2-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-aminofuran2_28-0">^</a></b></span> <span class="reference-text">Liu, P.; Lei, M.; Ma, L.; Hu, L. <i>Synlett</i> <b>2011</b>, <i>8</i>, 1133.</span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Stetter_reaction&oldid=1143768318">https://en.wikipedia.org/w/index.php?title=Stetter_reaction&oldid=1143768318</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Coupling_reactions" title="Category:Coupling reactions">Coupling reactions</a></li><li><a href="/wiki/Category:Addition_reactions" title="Category:Addition reactions">Addition reactions</a></li><li><a href="/wiki/Category:Carbon-carbon_bond_forming_reactions" title="Category:Carbon-carbon bond forming reactions">Carbon-carbon bond forming reactions</a></li><li><a href="/wiki/Category:Name_reactions" title="Category:Name reactions">Name reactions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 9 March 2023, at 19:34<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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