Enantioselective copper catalysed conjugate addition to 2- or 3- substituted cyclopent-2-ene-1-ones: Construction of stereogenic quaternary carbon centers

Vuagnoux-D'Augustin De, Magali; Kehrli, Stefan; Alexakis, Alexandre

doi:10.1055/s-2007-984889

Scientific article

Letter

English

Enantioselective copper catalysed conjugate addition to 2- or 3- substituted cyclopent-2-ene-1-ones: Construction of stereogenic quaternary carbon centers

ContributorsVuagnoux-D'Augustin De, Magali; Kehrli, Stefan; Alexakis, Alexandre

Published inSynlett, no. 13, p. 2057-2060

Publication date2007

Abstract

Trimethyl- and triethylaluminum undergo enantioselective conjugate addition to 2- and 3-substituted cyclopent-2-en-1- ones in the presence of catalytic amount of a copper salt and a phosphoramidite or a diphosphite ligand. Thus, chiral quaternary centers can be built with up to 93% ee.

Keywords

Aluminum
Copper
Michael addition
Asymmetric catalysis
Ligands

Affiliation

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

Citation (ISO format)

VUAGNOUX-D’AUGUSTIN DE, Magali, KEHRLI, Stefan, ALEXAKIS, Alexandre. Enantioselective copper catalysed conjugate addition to 2- or 3- substituted cyclopent-2-ene-1-ones: Construction of stereogenic quaternary carbon centers. In: Synlett, 2007, n° 13, p. 2057–2060. doi: 10.1055/s-2007-984889

Article (Published version)

Identifiers

PID : unige:8026
DOI : 10.1055/s-2007-984889

ISSN of the journal0936-5214

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Enantioselective copper catalysed conjugate addition to 2- or 3- substituted cyclopent-2-ene-1-ones: Construction of stereogenic quaternary carbon centers

Trimethyl- and triethylaluminum undergo enantioselective conjugate addition to 2- and 3-substituted cyclopent-2-en-1- ones in the presence of catalytic amount of a copper salt and a phosphoramidite or a diphosphite ligand. Thus, chiral quaternary centers can be built with up to 93% ee.

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