A Michael Addition and Peterson Olefination Sequence Using 1-Silylethenyl Sulfides and Sulfoxide

Article abstract of DOI:10.1246/bcsj.61.3957

Reaction of organolithiums with a 1-(trimethylsilyl)ethenyl sulfide produces 1,2-bis(trimethylsilyl)-cyclopropanes, while use of 1-silylethenyl sulfides bearing a bulkier silyl moiety results in exclusive formation of the corresponding Michael adducts anions which are then quenched with aldehydes to give vinyl sulfides.On the contrary, a 1-(trimethylsilyl)ethenyl sulfoxide undergoes smooth Michael addition with a variety of organometallics and the resulting carbanion intermediates can be quenched with aldehydes to produce vinyl sulfoxides.Scope and limitations of these sequential reactions are discussed.