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Scientific article
Letter
English

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

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).

Citation (ISO format)
VON OPPOLZER, Wolfgang et al. Enantiomerically pure, crystalline ‘anti”-aldols from <i>N</i>-acylbornanesultams: aldolization and structure of intermediate <i>t</i>-butyldimethylsilyl-<i>N,O</i>-ketene acetal. In: Tetrahedron Letters, 1991, vol. 32, n° 1, p. 61–64. doi: 10.1016/S0040-4039(00)71218-4
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ISSN of the journal0040-4039
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