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Synfacts 2007(4): 0404-0404  
DOI: 10.1055/s-2007-968364
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Addition of H-Phosphine Oxides to Alkynes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
M. Niu, H. Fu*, Y. Jiang, Y. Zhao
Tsinghua University, Beijing and Tsinghua University, Shenzhen, P. R. of China
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The authors describe the copper-catalyzed addition of H-phosphine oxides H(O)PR2 to alkynes to generate alkenyl phosphine oxides. The reaction produces E-alkenyl phosphine oxides under simple catalytic conditions using CuI/ethylenediamine. DMSO was determined to be the best solvent for this reaction and a variety of terminal or symmetrical alkynes all succeeded in generating the product regio- and stereoselectively.