Asymmetric additions of 1-alkenylcopper reagents to chiral enoates: enantioselective synthesis of california red scale pheromone

Von Oppolzer, Wolfgang; Stevenson, Thomas Martin

doi:10.1016/S0040-4039(00)84198-2

Scientific article

English

Asymmetric additions of 1-alkenylcopper reagents to chiral enoates: enantioselective synthesis of california red scale pheromone

ContributorsVon Oppolzer, Wolfgang; Stevenson, Thomas Martin

Published inTetrahedron letters, vol. 27, no. 10, p. 1139-1140

Publication date1986

Abstract

nBu₃P-stabilized 1-alkenylcopper reagents undergo efficient 1,4-additions to enoates 1 and 5. Thus, acids 3, 7 or alcohols 4, 8 were obtained in high e.e. with recovery of the auxiliary. 4d was converted to pure (-)-pheromone 13, and 8b gave bromide 14b.

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang, STEVENSON, Thomas Martin. Asymmetric additions of 1-alkenylcopper reagents to chiral enoates: enantioselective synthesis of california red scale pheromone. In: Tetrahedron letters, 1986, vol. 27, n° 10, p. 1139–1140. doi: 10.1016/S0040-4039(00)84198-2

Article (Published version)

Identifiers

PID : unige:167134
DOI : 10.1016/S0040-4039(00)84198-2

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900841982

Journal ISSN0040-4039

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Asymmetric additions of 1-alkenylcopper reagents to chiral enoates: enantioselective synthesis of california red scale pheromone

nBu3P-stabilized 1-alkenylcopper reagents undergo efficient 1,4-additions to enoates 1 and 5. Thus, acids 3, 7 or alcohols 4, 8 were obtained in high e.e. with recovery of the auxiliary. 4d was converted to pure (-)-pheromone 13, and 8b gave bromide 14b.

Technical informations

nBu₃P-stabilized 1-alkenylcopper reagents undergo efficient 1,4-additions to enoates 1 and 5. Thus, acids 3, 7 or alcohols 4, 8 were obtained in high e.e. with recovery of the auxiliary. 4d was converted to pure (-)-pheromone 13, and 8b gave bromide 14b.