Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols

Von Oppolzer, Wolfgang; Radinov, Roumen Nikolaev

doi:10.1016/S0040-4039(00)93553-6

Scientific article

Letter

English

Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols

ContributorsVon Oppolzer, Wolfgang; Radinov, Roumen Nikolaev

Published inTetrahedron Letters, vol. 32, no. 41, p. 5777-5780

Publication date1991

Abstract

In situ prepared (Z)- and (E)-1-alkenylzinc bromides 5 were added to various aldehydes 1 in the presence of lithiated (+)-N-methylephedrine or (+)-2-(N,N-dimethylamino)-1,2-diphenylethanol to give sec. allyalcohols 7 in high optical purity with simple recovery of the chiral aminol 6.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, RADINOV, Roumen Nikolaev. Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols. In: Tetrahedron Letters, 1991, vol. 32, n° 41, p. 5777–5780. doi: 10.1016/S0040-4039(00)93553-6

Article (Published version)

Identifiers

PID : unige:152454
DOI : 10.1016/S0040-4039(00)93553-6

Commercial URLhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900935536

ISSN of the journal0040-4039

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Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcohols

In situ prepared (Z)- and (E)-1-alkenylzinc bromides 5 were added to various aldehydes 1 in the presence of lithiated (+)-N-methylephedrine or (+)-2-(N,N-dimethylamino)-1,2-diphenylethanol to give sec. allyalcohols 7 in high optical purity with simple recovery of the chiral aminol 6.

Technical informations