An unexpected Prins desymmetrisation reaction driven by silyl migration

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