Desymmetrization of a meso-allylic acetal by enantioselective conjugate elimination.

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

doi:10.1021/ol702877j

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Desymmetrization of a meso-allylic acetal by enantioselective conjugate elimination.

Journal article

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Desymmetrization of a meso-allylic acetal by enantioselective conjugate elimination.

Ling Xu, Thomas Regnier, Loïc Lemiègre, Pascal Cardinael, Jean-Claude Combret, J.-P. Bouillon, Jérome Blanchet, Jacques Rouden, Anne Harrison-Marchand and Jacques Maddaluno

Organic Letters, Vol.10(5), pp.729-732

06/03/2008

DOI: https://doi.org/10.1021/ol702877j

PMID: 18254634

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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Title: Desymmetrization of a meso-allylic acetal by enantioselective conjugate elimination.
Creators - without role: Ling Xu - Institut National des Sciences Appliquées Rouen Normandie
Thomas Regnier - Université de Montpellier, Institut des Biomolécules Max Mousseron - IBMM
Loïc Lemiègre - Institut National des Sciences Appliquées Rouen Normandie
Pascal Cardinael - Institut National des Sciences Appliquées Rouen Normandie
Jean-Claude Combret - Sciences et Méthodes Séparatives
J.-P. Bouillon - Institut National des Sciences Appliquées Rouen Normandie
Jérome Blanchet - Université de Rouen Normandie
Jacques Rouden - Institut National des Sciences Appliquées Rouen Normandie
Anne Harrison-Marchand - Institut National des Sciences Appliquées Rouen Normandie
Jacques Maddaluno - Université de Rouen Normandie
Publication Details: Organic Letters, Vol.10(5), pp.729-732
Identifiers: 9938859509311
Academic Unit: Institut des Biomolécules Max Mousseron - IBMM
Language: English
Resource Type: Journal article
Local Fields: hal-00909869