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Synthesis 2011(12): 1968-1973  
DOI: 10.1055/s-0030-1260464
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Enantioselective Michael Addition of Ketones and an Aldehyde to Nitroalkenes Catalyzed by a Binaphthyl Sulfonimide in Water

Chunhua Luo, Da-Ming Du*
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, P. R. of China
e-Mail: dudm@bit.edu.cn;
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Publication History

Received 17 March 2011
Publication Date:
13 May 2011 (online)

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Abstract

A binaphthyl sulfonimide organocatalyst was used to promote highly enantioselective and diastereoselective Michael addition reactions of ketones to nitroalkenes in water. In most cases, the products were obtained in good yields with excellent enantioselectivities and diastereoselectivities (93-97% ee, up to >99:1 dr). The catalyst could also be used in an asymmetric Michael addition of isobutyraldehyde to nitroalkenes to give the desired products in moderate yields and moderate enantioselectivities (up to 83% ee).

Key words

asymmetric catalysis - organocatalysis - Michael additions - nitroalkenes - sulfonimides

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