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Synthesis 2008(23): 3828-3834  
DOI: 10.1055/s-0028-1083223
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Efficient and Recyclable Ionic Liquid Anchored Pyrrolidine Catalyst for Enantioselective Michael Additions

Tao Miaoa, Lei Wang*a,b, Pinhua Lia, Jincan Yana
a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
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Publication History

Received 24 July 2008
Publication Date:
14 November 2008 (online)

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Abstract

Highly enantioselective Michael addition of cyclohexanone to aryl nitroolefins in the presence of an ionic liquid anchored pyrrolidine (10 mol%) and TFA (5 mol%) generated the corresponding adducts in high yields (up to 95%) with excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to >99% ee). Furthermore, the catalyst could be recycled and reused at least eight times without loss of its catalytic activity.

Key words

chiral ionic liquid - pyrrolidine unit - organocatalyst - asymmetric Michael reaction - aryl nitroolefin - cyclohexanone

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