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Synfacts 2006(8): 0795-0795  
DOI: 10.1055/s-2006-942015
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Multicomponent Connection

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Kimura, K. Kojima, Y. Tatsuyama, Y. Tamaru*
Nagasaki University, Japan
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

The authors have devised a multicomponent reaction attaching alkynes, 1,3-butadiene, aldehydes, amines and dimethylzinc through nickel catalysis. Interestingly, the use of aromatic amines and aliphatic amines gives contrasting products with the former giving products incorporating one equivalent of 1,3-butadiene and the latter giving products with incorporation of two equivalents of 1,3-butadiene. Aromatic aldehydes with o- or p-substituents (electron-donating or -with­drawing) are tolerated and products are obtained with high yield and complete E/Z selectivity of the olefins.