Enantioselective nucleophilic opening of meso epoxides by organolithium reagents

Alexakis, Alexandre; Vrancken, Emmanuel; Mangeney, Pierre

doi:10.1055/s-1998-5741

Scientific article

English

Enantioselective nucleophilic opening of meso epoxides by organolithium reagents

ContributorsAlexakis, Alexandre; Vrancken, Emmanuel; Mangeney, Pierre

Published inSynlett, no. 10, p. 1165-1167

Publication date1998

Abstract

Aryl lithium reagents, complexed with (-)-sparteine, react enantioselectively with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiomeric excess, though moderate (27-87%), is the best in the literature for such a reaction. Activation by BF3 · OEt2 is needed, and is compatible with a diamine such as (-)-sparteine.

Keywords

epoxides
organolithium reagents
BF3 Et2O activation
(-)-sparteine

Affiliation Not a UNIGE publication

Citation (ISO format)

ALEXAKIS, Alexandre, VRANCKEN, Emmanuel, MANGENEY, Pierre. Enantioselective nucleophilic opening of meso epoxides by organolithium reagents. In: Synlett, 1998, n° 10, p. 1165–1167. doi: 10.1055/s-1998-5741

Article (Published version)

Identifiers

PID : unige:8156
DOI : 10.1055/s-1998-5741

ISSN of the journal0936-5214

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Enantioselective nucleophilic opening of meso epoxides by organolithium reagents

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