Preparation of Vinyl Allenes from 1-Lithio-1,3-dienyl Phosphine Oxides and Aldehydes by the Wittig−Horner Reaction

Zhenfeng Xi,*† Wen-Xiong Zhang,† Zhiyi Song,† Weixin Zheng,† Fanzhi Kong,† and Tamotsu Takahashi*‡
Peking University-Hokkaido University Joint Lab, College of Chemistry, Peking University, Beijing 100871, China, and Catalysis Research Center, Graduate School of Pharmaceutical Sciences, Hokkaido University and SORST, Japan Science and Technology Agency (JST), Kita-Ku, Sapporo 001-0021, Japan
J. Org. Chem., 2005, 70 (22), pp 8785–8789
DOI: 10.1021/jo051178c
Publication Date (Web): October 4, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Peking University.

,
‡

 Hokkaido University.

, zfxi@pku.edu.cn

Abstract

Abstract Image

Vinyl allenes were prepared in high yields by the Wittig−Horner reaction of 1-lithio-1,3-dienyl phosphine oxides with aldehydes. 1-Lithio-1,3-dienyl phosphine oxides were generated in situ from lithiation of 1-iodo-1,3-dienyl phosphine oxides, which were obtained by iodination of α-phosphinozirconacyclopentadienes. As a whole, a vinyl allene is synthesized from two different alkynes and one aldehyde.

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History

  • Published In Issue October 28, 2005
  • Received June 11, 2005

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