Copper catalyzed enantioselective allylic substitution by MeMgX

Tissot-Croset, Karine; Alexakis, Alexandre

doi:10.1016/j.tetlet.2004.07.114

Scientific article

Letter

English

Copper catalyzed enantioselective allylic substitution by MeMgX

ContributorsTissot-Croset, Karine; Alexakis, Alexandre

Published inTetrahedron letters, vol. 45, no. 39, p. 7375-7378

Publication date2004

Abstract

Methyl Grignard undergoes highly regio (>90/10) and enantioselective (ee 91–96%) copper catalyzed allylic substitution on cinnamyl-type chlorides. CuBr (3%) and 3.3% of a chiral phosphoramidite ligand are sufficient for a complete reaction. The synthesis of a precursor of (+)-Naproxen is described. The reaction can be extended to alkyl substituted allylic chlorides (ee 72%).

Keywords

Asymmetry
Copper
Catalysis
Grignard reagent
Allylic substitution
Naproxen

Affiliation

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

Citation (ISO format)

TISSOT-CROSET, Karine, ALEXAKIS, Alexandre. Copper catalyzed enantioselective allylic substitution by MeMgX. In: Tetrahedron letters, 2004, vol. 45, n° 39, p. 7375–7378. doi: 10.1016/j.tetlet.2004.07.114

Article (Published version)

Identifiers

PID : unige:8120
DOI : 10.1016/j.tetlet.2004.07.114

ISSN of the journal0040-4039

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Copper catalyzed enantioselective allylic substitution by MeMgX

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