Desymmetrization of a meso-Allylic
Acetal by Enantioselective Conjugate
Elimination

Xu, Ling; Regnier, Thomas; Lemiègre, Loïc; Cardinael, Pascal; Combret, Jean-Claude; Bouillon, Jean-Philippe; Blanchet, Jérome; Rouden, Jacques; Harrison-Marchand, Anne; Maddaluno, Jacques

doi:10.1021/ol702877j.s002

Desymmetrization of a meso-Allylic Acetal by Enantioselective Conjugate Elimination

journal contribution

posted on 2008-03-06, 00:00 authored by Ling Xu, Thomas Regnier, Loïc Lemiègre, Pascal Cardinael, Jean-Claude Combret, Jean-Philippe Bouillon, Jérome Blanchet, Jacques Rouden, Anne Harrison-Marchand, Jacques Maddaluno

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 °C in THF.