Synthesis 2012; 44(15): 2333-2339
DOI: 10.1055/s-0031-1290764
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Regio- and Stereoselective Multicomponent Coupling Reaction of Alkynes and Dimethylzinc Involving Allylnickelacycles

Takamichi Mori
Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   Email: [email protected]
,
Toshiyuki Nakamura
Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   Email: [email protected]
,
Gen Onodera
Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   Email: [email protected]
,
Masanari Kimura*
Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 10 February 2012

Accepted: 17 February 2012

Publication Date:
12 April 2012 (online)


Abstract

Nickel catalyzes the multicomponent coupling reaction of vinyl epoxides, alkynes, and dimethylzinc to provide hepta-2,5-dienyl alcohols as a mixture of E- and Z-isomers in high yields. Vinylcyclopropane participates in a similar multicomponent coupling reaction to afford dimethyl α-(hepta-2,5-dienyl)malonates with excellent E-stereoselectivity.

 
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