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Communication | Special issue | Vol 90, No. 2, 2015, pp.832-841
Published online, 2nd September, 2014
DOI: 10.3987/COM-14-S(K)65
■ Three-Component Coupling Reaction of Enynes, Carbonyls, and Organozinc Reagents

Yuki Ohira, Takamichi Mori, Maya Hayashi, Gen Onodera, and Masanari Kimura*

*Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

A mixture of t-butylzinc halide and an aldehyde reacts with enyne to provide homopropargyl alcohol in a 1,2-addition manner. Under carbon dioxide at atmospheric pressure, three components (t-butylzinc halide, enyne, and carbon dioxide) combine in a 1:1:1 ratio to give allenyl carboxylic acids in a 1,4-addition manner. These products are useful for the synthesis of heterocyclic compounds such as α,β-unsaturated γ-butyrolactones.