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Synthesis 2011(12): 1912-1917  
DOI: 10.1055/s-0030-1260527
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient and Modularly Tuned Bicyclic Organocatalyst for the Enantioselective Michael Addition of Aldehydes to Nitroalkenes

Jian Xiaoa,b, Feng-Xia Xua, Yun-Peng Lua, Yan-Ling Liua, Teck-Peng Loh*a
a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +65(679)11961; e-Mail: teckpeng@ntu.edu.sg;
b Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian, 116023, P. R. of China
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Publication History

Received 11 April 2011
Publication Date:
25 May 2011 (online)

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Abstract

A new type of bicyclic organocatalyst has been successfully applied to the asymmetric Michael addition of aldehydes to nitrostyrenes in good yields and good enantioselectivities by using a self-assembly strategy. The success of this reaction is attributed to good control of the geometry of the enamine and efficient face shielding.

Key words

organocatalyst - bicyclic - enamine control - Michael addition

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