Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams. Preliminary Communication

Von Oppolzer, Wolfgang; Mills, Robert John; Pachinger, Werner; Stevenson, Thomas Martin

doi:10.1002/hlca.19860690703

Scientific article

English

Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams. Preliminary Communication

ContributorsVon Oppolzer, Wolfgang; Mills, Robert John; Pachinger, Werner; Stevenson, Thomas Martin

Published inHelvetica chimica acta, vol. 69, no. 7, p. 1542-1545

Publication date1986-10-29

Abstract

EtAlCl2-promoted additions of organocopper reagents to camphor-derived, conjugated N-enoyl-sultams gave saturated and olefinic β-silylcarboxyl derivatives with high diastereodifferentiation. Nondestructive removal of the chiral auxiliary followed by oxidative Si-C bond cleavage furnished enantiomerically pure acetate-derived aldols and propionate-derived ‘anti' -aldols (via silyl-directed α-methylation).

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams. Preliminary Communication. In: Helvetica chimica acta, 1986, vol. 69, n° 7, p. 1542–1545. doi: 10.1002/hlca.19860690703

Article (Published version)

Identifiers

PID : unige:156115
DOI : 10.1002/hlca.19860690703

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19860690703

Journal ISSN0018-019X

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Preparation of Enantiomerically Pure β-Silylcarboxyl Derivatives by Asymmetric 1,4-Addition to N-Enoyl-sultams. Preliminary Communication

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