Enantioselective copper-catalyzed SN2' substitution with Grignard reagents

Alexakis, Alexandre; Malan, Christophe; Lea, Louise Sarah; Benhaim, Cyril; Fournioux, Xavier

doi:10.1055/s-2001-14626

Scientific article

English

Enantioselective copper-catalyzed SN2' substitution with Grignard reagents

ContributorsAlexakis, Alexandre; Malan, Christophe; Lea, Louise Sarah; Benhaim, Cyril; Fournioux, Xavier

Published inSynlett, no. Special issue, p. 927-930

Publication date2001

Abstract

Cinnamyl chlorides undergo selective SN2´ allylic substitution by Grignard reagents using catalytic amount (1 mol%) of CuCN and 1-2 mol% trivalent phosphorus ligands, in dichloromethane. With chiral phosphorus ligands derived from TADDOL ee's up to 73% could be obtained.

Keywords

154 SN2%27 Asym Synlett 01.pdf
Chiral phosphorus ligands
Copper
Asymmetric catalysis
SN2´
TADDOL

Affiliation entities

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

Citation (ISO format)

ALEXAKIS, Alexandre et al. Enantioselective copper-catalyzed SN2′ substitution with Grignard reagents. In: Synlett, 2001, n° Special issue, p. 927–930. doi: 10.1055/s-2001-14626

Article (Published version)

Identifiers

PID : unige:8155
DOI : 10.1055/s-2001-14626

ISSN of the journal0936-5214

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Enantioselective copper-catalyzed SN2' substitution with Grignard reagents

Cinnamyl chlorides undergo selective SN2´ allylic substitution by Grignard reagents using catalytic amount (1 mol%) of CuCN and 1-2 mol% trivalent phosphorus ligands, in dichloromethane. With chiral phosphorus ligands derived from TADDOL ee's up to 73% could be obtained.

Technical informations