Organolithium chiral Lewis base BF3 : versatile combination for the enantioselective desymmetrisation of meso-epoxides

Vrancken, Emmanuel; Alexakis, Alexandre; Mangeney, Pierre

doi:10.1002/ejoc.200400745

Scientific article

English

Organolithium chiral Lewis base BF3 : versatile combination for the enantioselective desymmetrisation of meso-epoxides

ContributorsVrancken, Emmanuel; Alexakis, Alexandre; Mangeney, Pierre

Published inEuropean journal of organic chemistry, vol. 2005, no. 7, p. 1354-1366

Publication date2005

Abstract

BF3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring-opening or the carbenoidic rearrangement of various meso-oxiranes with excellent yields and ee values of up to 87 %. Mechanistic aspects of these reactions are considered.

Keywords

Boranes
Carbenoids
Lithium
Lewis bases
Synthetic methods

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VRANCKEN, Emmanuel, ALEXAKIS, Alexandre, MANGENEY, Pierre. Organolithium chiral Lewis base BF3 : versatile combination for the enantioselective desymmetrisation of meso-epoxides. In: European journal of organic chemistry, 2005, vol. 2005, n° 7, p. 1354–1366. doi: 10.1002/ejoc.200400745

Article (Published version)

Identifiers

PID : unige:8034
DOI : 10.1002/ejoc.200400745

Journal ISSN1099-0690

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Organolithium chiral Lewis base BF3 : versatile combination for the enantioselective desymmetrisation of meso-epoxides

BF3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring-opening or the carbenoidic rearrangement of various meso-oxiranes with excellent yields and ee values of up to 87 %. Mechanistic aspects of these reactions are considered.

Technical informations