Issue 21, 2003

Ene cyclisations of α-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols

Abstract

A variety of routes are described for the synthesis of α-silyloxy aldehydes in which the silicon atom bears a prenyl side chain. These compounds are shown to undergo stereoselective carbonyl ene cyclisation under mildly Lewis acidic conditions and the derived silacycles are cleaved to afford single diastereomers of functionalised triols.

Graphical abstract: Ene cyclisations of α-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols

Supplementary files

Article information

Article type
Paper
Submitted
17 Jun 2003
Accepted
04 Aug 2003
First published
10 Sep 2003

Org. Biomol. Chem., 2003,1, 3758-3767

Ene cyclisations of α-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols

J. Robertson, M. J. Hall, P. M. Stafford and S. P. Green, Org. Biomol. Chem., 2003, 1, 3758 DOI: 10.1039/B306922M

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