Chiral Pyrrolidine Sulfonamide
Catalyzed Enantioselective Michael Addition of Cyclohexanones to
Maleimides

Jian Wang; Man-Man Zhang; Shieli Zhang; Zi-An Xu; Hao Li; Xin-Hong Yu; Wei Wang

doi:10.1055/s-0030-1259517

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Synlett 2011(4): 473-476
DOI: 10.1055/s-0030-1259517

CLUSTER

Chiral Pyrrolidine Sulfonamide Catalyzed Enantioselective Michael Addition of Cyclohexanones to Maleimides

Jian Wang^a, Man-Man Zhang^b, Shieli Zhang^a, Zi-An Xu^b, Hao Li^c, Xin-Hong Yu*^b, Wei Wang*^a,b,c
^a Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA
Fax: +1(505)2772609; e-Mail: wwang@unm.edu;
^b Department of Medicinal Chemistry, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, P. R. of China
e-Mail: xhyu@ecust.edu.cn;
^c Shanghai Institute of Materia Medica, Shanghai Institutes of Biological Sciences, Chinese Academy of Sciences, Graduate School of the Chinese Academy of Sciences, Shanghai 201203, P. R. of China

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Publication History

Received 20 November 2010
Publication Date:
27 January 2011 (online)

Abstract
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Abstract

An organocatalytic enantioselective conjugate addition of cyclohexanones to maleimides has been developed. The process catalyzed by a (S)-pyrrolidine sulfonamide affords synthetically and medicinally useful chiral succinimides under mild reaction conditions.

Key words

cyclic ketones - maleimides - Michael reaction - pyrrolidine sulfonamide

Supporting Information

References and Notes

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CCDC-664491 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk.

Supplementary Material

Supporting Information