A Michael Addition and Peterson Olefination Sequence Using 1-Silylethenyl Sulfides and Sulfoxide
- 1 November 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 61 (11) , 3957-3964
- https://doi.org/10.1246/bcsj.61.3957
Abstract
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 adduct 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 organo-metallics and the resulting carbanion intermediates can be quenched with aldehydes to produce vinyl sulfoxides. Scope and limitations of these sequential reactions are discussed.Keywords
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