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

Tao Miao; Lei Wang; Pinhua Li; Jincan Yan

doi:10.1055/s-0028-1083223

PAPER

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

Tao Miao^a, Lei Wang*^a,b, Pinhua Li^a, Jincan Yan^a
^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;

Abstract

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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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