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Synfacts 2009(6): 0638-0638  
DOI: 10.1055/s-0029-1217152
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Phospha-Michael Addition of Enones

Contributor(s): Mark Lautens, Praew Thansandote
D. Zhao, Y. Yuan, A. S. C. Chan, R. Wang*
Lanzhou University and The Hong Kong Polytechnic University, P. R. of China
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

The first example of an asymmetric 1,4-addition of diethyl phosphite with simple enones using a dinuclear zinc catalyst is reported. A variety of substituted enones can be used for the reaction resulting in excellent yields and enantioselectivities for the phospha-Michael products. Switching from diethyl phosphite to phosphites with bulkier groups resulted in lower yields and ee values.