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<!DOCTYPE html><html><head><title>Organolithiums: Selectivity for Synthesis - Jonathan Clayden - Google Books</title><link rel="stylesheet" href="/books/css/_a33f2a89320471e58c940b9287b9d4eb/kl_viewport_kennedy_full_bundle.css" type="text/css" /><link rel="stylesheet"href="https://fonts.googleapis.com/css2?family=Product+Sans:wght@400"><script src="/books/javascript/v2_a33f2a89320471e58c940b9287b9d4eb__en.js"></script><script>_OC_Hooks = ["_OC_Page", "_OC_SearchReload", "_OC_TocReload", "_OC_EmptyFunc", "_OC_SearchPage", "_OC_QuotePage" ];for (var _OC_i = 0; _OC_i < _OC_Hooks.length; _OC_i++) {eval("var " + _OC_Hooks[_OC_i] + ";");}function _OC_InitHooks () {for (var i = 0; i < _OC_Hooks.length; i++) {var func = arguments[i];eval( _OC_Hooks[i] + " = func;");}}</script><link rel="canonical" href="https://books.google.com/books/about/Organolithiums.html?id=4d58jpyx1AgC"/><meta property="og:url" content="https://books.google.com/books/about/Organolithiums.html?id=4d58jpyx1AgC"/><meta name="title" content="Organolithiums"/><meta name="description" content="This volume, number 23 in the "Tetrahedron Organic Chemistry" series, presents organolithium chemistry from the perspective of a synthetic organic chemist, drawing from the synthetic literature to present a unified overview of how organolithiums can be used to make molecules. The development of methods for the regioselective synthesis of organolithiums has replaced their image of indiscriminate high reactivity with one of controllable and subtle selectivity. Organolithium chemistry has a central role in the selective construction of C-C bonds in both simple and complex molecules, and for example has arguably overtaken aromatic electrophilic substitution as the most powerful method for regioselective functionalisation of aromatic rings. The twin themes of reactivity and selectivity run through the book, which reviews the ways by which organolithiums may be formed and the ways in which they react. 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The development of methods for the regioselective synthesis of organolithiums has replaced their image of indiscriminate high reactivity with one of controllable and subtle selectivity. Organolithium chemistry has a central role in the selective construction of C-C bonds in both simple and complex molecules, and for example has arguably overtaken aromatic electrophilic substitution as the most powerful method for regioselective functionalisation of aromatic rings. The twin themes of reactivity and selectivity run through the book, which reviews the ways by which organolithiums may be formed and the ways in which they react. Topics include advances in directed metallation, reductive lithiation and organolithium cyclisation reactions, along with a discussion of organolithium stereochemistry and the role played by ligands such as (-)-sparteine.","my_library_url":"https://www.google.com/accounts/Login?service=print\u0026continue=https://books.google.com.sg/books%3Fop%3Dlibrary\u0026hl=en","is_magazine":false,"is_public_domain":false},{"enableUserFeedbackUI":true,"pseudocontinuous":true,"is_cobrand":false,"sign_in_url":"https://www.google.com/accounts/Login?service=print\u0026continue=https://books.google.com.sg/books%3Fid%3D4d58jpyx1AgC%26pg%3DPA166%26dq%3DYus%26hl%3Den%26sa%3DX\u0026hl=en","isEntityPageViewport":false,"showViewportOnboarding":false,"showViewportPlainTextOnboarding":false},{"page":[{"pid":"PA166","highlights":[{"X":163,"Y":167,"W":21,"H":12},{"X":199,"Y":338,"W":20,"H":11},{"X":199,"Y":353,"W":21,"H":11},{"X":217,"Y":385,"W":20,"H":12},{"X":217,"Y":400,"W":21,"H":12},{"X":318,"Y":416,"W":20,"H":12},{"X":150,"Y":447,"W":20,"H":12},{"X":303,"Y":463,"W":20,"H":12},{"X":321,"Y":478,"W":20,"H":12},{"X":92,"Y":509,"W":21,"H":12},{"X":93,"Y":525,"W":21,"H":11},{"X":223,"Y":540,"W":21,"H":11},{"X":217,"Y":556,"W":20,"H":11},{"X":165,"Y":572,"W":21,"H":11},{"X":232,"Y":586,"W":20,"H":13},{"X":160,"Y":618,"W":20,"H":13},{"X":160,"Y":634,"W":21,"H":12},{"X":160,"Y":649,"W":21,"H":12},{"X":284,"Y":665,"W":20,"H":12},{"X":165,"Y":680,"W":21,"H":11}],"flags":8,"order":185,"vq":"Yus"}]},null,{"number_of_results":7,"search_results":[{"page_id":"PA8","page_number":"8","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M .; Seebach , D. Helv . Chim . Acta 1984 , 67 , 289 . Hoffmann , R. W .; Kemper , B. Tetrahedron Lett . 1981 , 22 , 5263 . Hay , D. R .; Song , Z .; Smith , S. G .; Beak , P. J. Am . Chem . Soc . 1988 , 110 , 8145 . Screttas , C\u0026nbsp;..."},{"page_id":"PA99","page_number":"99","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M .; Foubelo , F. J. Chem . Soc . , Perkin Trans . I 1994 , 1069 . 121 . 122 . 123 . 124 . 125 . Kirby , A. J .; Percy , J. M. Tetrahedron 1988 , 44 , 6903 . 126 . Kiefl , C .; Mannschreck , A. Synthesis 1995 , 1033 . Narasimhan\u0026nbsp;..."},{"page_id":"PA152","page_number":"152","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e showed that reductive lithation with naphthalene was nonetheless an effective way of making functionalised organolithiums . The ẞ - oxygenated species such as 11 are stable below -78 ° C provided the lithium is at a primary centre\u0026nbsp;..."},{"page_id":"PA166","page_number":"166","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M. Eur . J. Org . Chem . 2000 , 225 . 10 . Screttas , C. G. J. Chem . Soc . , Chem . Commun . 1972 , 752 . 11 ... \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron Lett . 1998 , 39 , 1397 . Gómez , C .; Ruiz , S .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron 1999 , 55 , 7017\u0026nbsp;..."},{"page_id":"PA167","page_number":"167","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron 1995 , 51 , 11457 . Guijarro , D .; Mancheño , B .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron 1995 , 48 , 4593 . Alonso , E .; Ramón , D. J .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron 1996 , 52 , 14341 . Bachki , A .; Foubelo , F .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron\u0026nbsp;..."},{"page_id":"PA168","page_number":"168","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M. Synlett 1997 , 491 . Alonso , D. A .; Alonso , E .; Nájera , C .; Ramón , D. J .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron 1997 , 53 , 4835 . Guijarro , D .; \u003cb\u003eYus\u003c/b\u003e , M. Tetrahedron Lett . 1994 , 35 , 2965 . Alonso , E .; Guijarro , D .; \u003cb\u003eYus\u003c/b\u003e , M\u0026nbsp;..."},{"page_id":"PA239","page_number":"239","snippet_text":"... \u003cb\u003eYus\u003c/b\u003e , M. J. Org . Chem . 1994 , 59 , 3210 . Kato , T .; Marumoto , S .; Sato , T .; Kuwajima , I. Synlett 1990 , 671 . Marsch , M .; Harms , K .; Zschage , O .; Hoppe , D .; Boche , G. Angew . Chem . , Int . Ed . Engl . 1991 , 103 , 321\u0026nbsp;..."}],"search_query_escaped":"Yus"},{});</script></div></div></div><script>(function() {var href = window.location.href;if (href.indexOf('?') !== -1) {var parameters = href.split('?')[1].split('&');for (var i = 0; i < parameters.length; i++) {var param = parameters[i].split('=');if (param[0] == 'focus') {var elem = document.getElementById(param[1]);if (elem) {elem.focus();}}}}})();</script>