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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, Email: zfxipku.edu.cn

Z. Xi, W.-X. Zhang, Z. Song, W. Zheng, F. Kong, T. Takahashi, J. Org. Chem., 2005, 70, 8785-8789.

DOI: 10.1021/jo051178c (free Supporting Information)


Abstract

Lithiation of 1-iodo-1,3-dienyl phosphine oxides and subsequent Wittig-Horner reaction with aldehydes gives vinyl allenes in high yields. The preparation of the 1-iodo-1,3-dienyl phosphine oxides is described. This multi-step sequence allows the synthesis of vinyl allenes from two different alkynes and one aldehyde.

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Key Words

Wittig-Horner Reaction, Allenes, Vinyl iodides


ID: J42-Y2005-1710