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Synthesis 2004(18): 3089-3091  
DOI: 10.1055/s-2004-834908
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© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,ω-Ene-Diene, and Acetone: Synthesis of 1,2-Disubstituted Cycloalkanes

Masanari Kimuraa, Keisuke Kojimab, Yoshinao Tamaru*b
a Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan
b Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan
Fax: +81(958)192677; e-Mail: tamaru@net.nagasaki-u.ac.jp;
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Publication History

Received 28 September 2004
Publication Date:
08 November 2004 (online)

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Abstract

Under nickel catalysis, 1,3,8-nonatrienes and 1,3,9-deca­trienes 3 react at room temperature with dimethylzinc and acetone at the alkene and diene termini, respectively, providing 1,2-disubstituted cycloalkanes 4 in good yield. The stereoselectivities of 4 provide useful information about the mechanistic frameworks for the present reaction and related cyclization reaction of ω-dienynes 1.

Keywords

nickel - organozinc - catalysis - cyclization - diene

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