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Synfacts 2010(6): 0714-0714  
DOI: 10.1055/s-0029-1219999
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Michael Reaction Catalyzed by Chiral Thiophosphoramidate

Contributor(s): Benjamin List, Ji-Woong Lee
A. Lu, R. Wu, Y. Wang*, Z. Zhou*, G. Wu, J. Fang, C. Tang
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

The authors report a highly efficient thiophosphoramidate bifunctional catalyst 1a based on the pyrrolidine backbone for the Michael reaction of ketones to nitroolefins. Various nitro-olefins are tolerated with excellent diastereoselectivity and enantioselectivity. Inferior catalytic performance was observed by using an oxo analogue 1b which might be related to its acidity.

Review: S. B. Tsogoeva Eur. J. Org. Chem. 2007, 1701-1716.