Asymmetric 1,4-additions of coordinated MeCu.BF<sub>3</sub> to chiral enoates: enantioselective syntheses of (S)-(−)-citronellic acid

Von Oppolzer, Wolfgang; Moretti, Robert; Godel, Thierry; Meunier, Anne Marie Yvonne; Loeher, Heinz Joséf

doi:10.1016/S0040-4039(01)99824-7

Scientific article

Letter

English

Asymmetric 1,4-additions of coordinated MeCu.BF₃ to chiral enoates: enantioselective syntheses of (S)-(−)-citronellic acid

ContributorsVon Oppolzer, Wolfgang; Moretti, Robert; Godel, Thierry; Meunier, Anne Marie Yvonne; Loeher, Heinz Joséf

Published inTetrahedron letters, vol. 24, no. 45, p. 4971-4974

Publication date1983

Abstract

nBu₃P- or cyanide-stabilized RCu.BF₃ (R-Me, 4-Me-3-pentenyl) undergo efficient 1,4-additions to neopentylether-shielded trans-enoates. Thus chiral β-substituted carboxylic acids e.g. (S)-citronellic acid were obtained in high e.e. (Schemes 2 and 4).

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Asymmetric 1,4-additions of coordinated MeCu.BF₃ to chiral enoates: enantioselective syntheses of (S)-(−)-citronellic acid. In: Tetrahedron letters, 1983, vol. 24, n° 45, p. 4971–4974. doi: 10.1016/S0040-4039(01)99824-7

Article (Published version)

Identifiers

PID : unige:168187
DOI : 10.1016/S0040-4039(01)99824-7

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901998247

Journal ISSN0040-4039

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Asymmetric 1,4-additions of coordinated MeCu.BF3 to chiral enoates: enantioselective syntheses of (S)-(−)-citronellic acid

nBu3P- or cyanide-stabilized RCu.BF3 (R-Me, 4-Me-3-pentenyl) undergo efficient 1,4-additions to neopentylether-shielded trans-enoates. Thus chiral β-substituted carboxylic acids e.g. (S)-citronellic acid were obtained in high e.e. (Schemes 2 and 4).

Technical informations

Asymmetric 1,4-additions of coordinated MeCu.BF₃ to chiral enoates: enantioselective syntheses of (S)-(−)-citronellic acid

nBu₃P- or cyanide-stabilized RCu.BF₃ (R-Me, 4-Me-3-pentenyl) undergo efficient 1,4-additions to neopentylether-shielded trans-enoates. Thus chiral β-substituted carboxylic acids e.g. (S)-citronellic acid were obtained in high e.e. (Schemes 2 and 4).