Asymmetric Michael addition of a chiral ester-dienolate: enantioselective synthesis of (−)-khusimone

Von Oppolzer, Wolfgang; Pitteloud, Rita; Bernardinelli, Gérald Hugues; Baettig, Kurt

doi:10.1016/S0040-4039(01)99825-9

Scientific article

Letter

English

Asymmetric Michael addition of a chiral ester-dienolate: enantioselective synthesis of (−)-khusimone

ContributorsVon Oppolzer, Wolfgang; Pitteloud, Rita; Bernardinelli, Gérald Hugues; Baettig, Kurt

Published inTetrahedron letters, vol. 24, no. 45, p. 4975-4978

Publication date1983

Abstract

A double π-face-selective aprotic Michael addition of the lithium dienolate derived from the chiral senecioate 2b to cyclopentenone coupled with recovery of the auxiliary 14 serves for the enantioselective synthesis of (−)-khusimone (12) (Schemes 1 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 Michael addition of a chiral ester-dienolate: enantioselective synthesis of (−)-khusimone. In: Tetrahedron letters, 1983, vol. 24, n° 45, p. 4975–4978. doi: 10.1016/S0040-4039(01)99825-9

Article (Published version)

Identifiers

PID : unige:168184
DOI : 10.1016/S0040-4039(01)99825-9

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403901998259

Journal ISSN0040-4039

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Asymmetric Michael addition of a chiral ester-dienolate: enantioselective synthesis of (−)-khusimone

A double π-face-selective aprotic Michael addition of the lithium dienolate derived from the chiral senecioate 2b to cyclopentenone coupled with recovery of the auxiliary 14 serves for the enantioselective synthesis of (−)-khusimone (12) (Schemes 1 and 4).

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