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According to the protocol for the acetalization-intramolecular allylsilane cyclization, a new enantioenriched allylsilane, (R)-(E)-7-(dimethylphenylsilyl)undec-5-en-1-ol, in the presence of a variety of aldehydes provided enantioenriched trans-2,3-disubstituted oxepanes stereoselectively.

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Intramolecular cyclizations of optically active allylsilanes bearing electrophilic functional groups on their a-alkyl side chains were examined. The allylsilanes having aldehyde and enone functional groups underwent the intramolecular cyclizations in the presence of Lewis acid catalysts to give 6-and 7-membered cycloalkenes with high stereoselectivity in good yields. Reactions of the allylsilanes having a-hydroxyalkyl chain with aldehydes provided 6-and 7-membered oxacycloalk-4-enes stereoselectively in good yields. Use of highly enantioenriched allylsilanes furnished enantioenriched cyclic alkenes with almost perfect chirality transfer from the allylsilanes.