Ene cyclisations of alpha-(prenyl)dialkylsilyloxy aldehydes: formation and oxidative cleavage of oxasilacyclohexanols.
A variety of routes are described for the synthesis of a-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.
Robertson
Jeremy
J
Dyson Perrins Laboratory, South Parks Road, Oxford, UK OX1 3QY.
Hall
Michael J
MJ
Stafford
Petra M
PM
Green
Stuart P
SP