Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

Kehrli, Stefan; Martin, David; Rix, Diane; Mauduit, Marc; Alexakis, Alexandre

doi:10.1002/chem.201000471

Scientific article

English

Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

ContributorsKehrli, Stefan; Martin, David; Rix, Diane; Mauduit, Marc; Alexakis, Alexandre

Published inChemistry, vol. 16, no. 32, p. 9890-9904

Publication date2010

Abstract

The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as efficient chiral ligands for this transformation. High enantioselectivities (up to 96 % ee) could be obtained for a variety of substrates.

Keywords

Asymmetry
Conjugate addition
Copper
Grignard reaction
N-heterocyclic carbenes

Affiliation entities

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

Citation (ISO format)

KEHRLI, Stefan et al. Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones. In: Chemistry, 2010, vol. 16, n° 32, p. 9890–9904. doi: 10.1002/chem.201000471

Article (Published version)

Identifiers

PID : unige:11963
DOI : 10.1002/chem.201000471

Journal ISSN0947-6539

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Creation30/09/2010 11:14:00

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Formation of Quaternary Chiral Centers by N-Heterocyclic Carbene-Cu-Catalyzed Asymmetric Conjugate Addition Reactions with Grignard Reagents on Trisubstituted Cyclic Enones

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