An unexpected Prins desymmetrisation reaction driven by silyl migration

M Butters, MC Elliott, JT Hill-Cousins

Index: Butters, Michael; Elliott, Mark C; Hill-Cousins, Joseph T. Arkivoc, 2012 , vol. 2012, # 7 p. 113 - 125

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Abstract

Prins desymmetrisation reactions of cyclohexa-1, 4-diene derivatives have been investigated as a route to the core of the cladiellin diterpenes. During the course of this work, we observed the formation of a partially-reduced benzofuran 18, which is clearly derived from oxocarbenium ion 21. This can only be rationalised by an unexpected primary to secondary silyl group migration.