Intramolecular ene reaction of epoxyallylsilanes: synthesis of allyl- and vinylsilane-functionalized cyclohexanols.

Abstract

[reaction: see text] Epoxyallylsilanes bearing the bulky tert-butyldiphenylsilyl group undergo an uncommon tandem rearrangement-cyclization process upon treatment with Lewis acids. Two pathways for the carbonyl ene reaction are observed: one leading to allylsilane-cyclohexanols when the epoxyallylsilane (28-31) is nonsubstituted, 2-, or 4-monosubstituted… (More)

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