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Desymmetrization of a meso-allylic acetal by enantioselective conjugate elimination |
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| Authors: | Xu Ling Regnier Thomas Lemiègre Loïc Cardinael Pascal Combret Jean-Claude Bouillon Jean-Philippe Blanchet Jérome Rouden Jacques Harrison-Marchand Anne Maddaluno Jacques |
| Institution: | Laboratoire des Fonctions Azotées et Oxygénées Complexes de l'IRCOF, UMR CNRS 6014, Université et INSA de Rouen, 76821 Mont Saint-Aignan Cedex, France. |
| Abstract: | An unprecedented enantioselective deprotonation/conjugate elimination sequence, which transforms an allylic meso-dioxepane into a chiral diene, is described. The best desymmetrization conditions (ee up to 70%) involve s-BuLi and sparteine at -78 degrees C in THF. |
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