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

Lookup NU author(s): Dr Michael HallORCiD

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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.

Publication metadata

Author(s): Hall MJ; Robertson J; Stafford PM; Green SP

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2003

Volume: 1

Issue: 21

Pages: 3758-3767

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b306922m

DOI: 10.1039/b306922m

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