Enantiomerically pure, crystalline ‘anti'-aldols from N-acylbornanesultams: aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal

Von Oppolzer, Wolfgang; Starkemann, Christian; Rodriguez, Ines; Bernardinelli, Gérald Hugues

doi:10.1016/S0040-4039(00)71218-4

Scientific article

Letter

English

Enantiomerically pure, crystalline ‘anti'-aldols from N-acylbornanesultams: aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal

ContributorsVon Oppolzer, Wolfgang; Starkemann, Christian; Rodriguez, Ines; Bernardinelli, Gérald Hugues

Published inTetrahedron Letters, vol. 32, no. 1, p. 61-64

Publication date1991

Abstract

O-Silylation of N-propionylsultam 1 provides pure Z O-silyl-N,O-ketene acetal 2 which undergoes Lewis acid promoted addition of aromatic and aliphatic aldehydes to give diastereomerically pure, crystalline “anti” aldols 7 or their silylethers 3. Hydroperoxide-assisted hydrolysis/esterification of products 7 yields enantiomerically pure methoxycarbonyl aldols (11,12,13,14).

Affiliation entities

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

Citation (ISO format)

VON OPPOLZER, Wolfgang et al. Enantiomerically pure, crystalline ‘anti”-aldols from N-acylbornanesultams: aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal. In: Tetrahedron Letters, 1991, vol. 32, n° 1, p. 61–64. doi: 10.1016/S0040-4039(00)71218-4

Article (Published version)

Identifiers

PID : unige:152456
DOI : 10.1016/S0040-4039(00)71218-4

Additional URL for this publicationhttps://linkinghub.elsevier.com/retrieve/pii/S0040403900712184

Journal ISSN0040-4039

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Enantiomerically pure, crystalline ‘anti'-aldols from N-acylbornanesultams: aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal

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