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Scientific article
English

Bornanesultam-Directed Asymmetric Synthesis of Crystalline, Enantiomerically Pure Syn Aldols

Published inJournal of the American Chemical Society, vol. 112, no. 7, p. 2767-2772
Publication date1990
Abstract

N-acylsultams 2 furnish, via aldolization of their enolates 16 with aldehydes, diastereomerically pure, crystalline syn aldols. The absolute configuration of the product is controlled by the choice of the enolate counterion: 16, M = B → 3; 16, M = Li or Sn(IV) → 5. Hydroperoxide-assisted hydrolysis/esterification or reductive cleavage provided enantiomerically pure methoxycarbonyl aldols (12 and 13) or 1,3-diols (11) with recovery of auxiliary 1. The chiral serricornin precursor 14 was thus prepared.

Citation (ISO format)
VON OPPOLZER, Wolfgang et al. Bornanesultam-Directed Asymmetric Synthesis of Crystalline, Enantiomerically Pure Syn Aldols. In: Journal of the American Chemical Society, 1990, vol. 112, n° 7, p. 2767–2772. doi: 10.1021/ja00163a045
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ISSN of the journal0002-7863
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