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Paper | Special issue | Vol 42, No. 2, 1996, pp.565-575
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S22
Carbometalation of Cyclopropenes. Seteroselective Synthesis of Divinyl Ketones via 1,5-Hydrogen Migration Reaction of Vunylcyclopropanes

Katsumi Kubota, Masahiko Isaka, and Eiichi Nakamura

*Department of Chemistry, Tokyo Instituteof Technology, Meguro-ku, Tokyo 152-8552, Japan

Abstract

Stereoselective addition of a vinyl cuprate reagent to a cyclopropenone acetal (2) followed by in situ electrophilic trapping with an alkylating agent affords a cis-1-alkyl-2-vinylcyclopropanone acetal (3), which then undergoes thermal 1,5-hydrogen migration reaction to give the acetal of a Z,E-dienone (4) in 70-90% overall yield. Hydrolysis under mild acidic conditions affords the corresponding dienone or trienone (5) in high yield.