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

Authors

  • Takamichi Mori

    Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   eMail: masanari@nagasaki-u.ac.jp
  • Toshiyuki Nakamura

    Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   eMail: masanari@nagasaki-u.ac.jp
  • Gen Onodera

    Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   eMail: masanari@nagasaki-u.ac.jp
  • Masanari Kimura*

    Graduate School of Engineering, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan, Fax: +81(95)8192677   eMail: masanari@nagasaki-u.ac.jp
Weitere Informationen

Publikationsverlauf

Received: 10. Februar 2012

Accepted: 17. Februar 2012

Publikationsdatum:
12. April 2012 (online)


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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.