Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes

Shanchao Wu; Yu Li; Yongqiang Zhang; Kun Fang; Guoqiang Dong; Na Liu; Zhenyuan Miao; Jianzhong Yao; Wei Wang; Wannian Zhang; Chunquan Sheng

doi:10.1039/C5OB02457A

Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes†

Shanchao Wu,‡^a Yu Li,‡^a Yongqiang Zhang,^ab Kun Fang,^a Guoqiang Dong,^a Na Liu,^a Zhenyuan Miao,^a Jianzhong Yao,^a Wei Wang,*^bc Wannian Zhang*^a and Chunquan Sheng*^a

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^a Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, P. R. China
E-mail: zhangwnk@hotmail.com, shengcq@hotmail.com
Fax: +86-21-8187124
Tel: +86-21-8187124

^b School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China

^c Department of Chemistry and Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA
E-mail: wwang@unm.edu
Fax: +(505) 277-2609
Tel: +(505) 277-0756

Abstract

The Michael reaction of substituted isorhodanines with α,β-unsaturated aldehydes in the presence of a catalytic amount of a chiral secondary amine is presented. This transformation proceeds in good to high yields furnishing the corresponding 4,5-disubstituted isorhodanine adducts in good to excellent enantioselectivities.

This article is part of the themed collection: Contemporary Synthetic Chemistry in Drug Discovery

Organic & Biomolecular Chemistry

Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes†

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Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes

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