A highly enantioselective Michael reaction between α,β-unsaturated ketones and malonic acid half-thioesters

Qiao Ren; Tao Gao; Wenjun Li; Li Wan; Yimin Hu; Yanhong Peng; Shaofa Sun; Liqiang Hu; Minghu Wu; Haibing Guo; Jian Wang

doi:10.1039/C5NJ00719D

A highly enantioselective Michael reaction between α,β-unsaturated ketones and malonic acid half-thioesters†

Qiao Ren,‡^a Tao Gao,‡^b Wenjun Li,‡^a Li Wan,^b Yimin Hu,^b Yanhong Peng,^b Shaofa Sun,*^b Liqiang Hu,^b Minghu Wu,^b Haibing Guo*^b and Jian Wang*^a

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* Corresponding authors

^a Department of Chemistry, National University of Singapore, Block S15, Level 5, 3 Science Drive 3, Singapore 117543, Singapore
E-mail: wangjian1999@hotmail.com
Fax: +65-6779-1691

^b Hubei Collaborative Innovation Centre for Non-power Nuclear Technology, College of Chemistry and Biological Sciences, Hubei University of Science and Technology, Hubei Province 437100, People's Republic of China
E-mail: 1047470997@qq.com

Abstract

We disclose herein an efficient enantioselective organocatalytic Michael reaction between α,β-unsaturated ketones and malonic acid half thioesters (MAHTs). The reactions are catalyzed by a primary amine to generate Michael addition products in good to excellent yields (62–87%) with high to excellent enantioselectivities (80–98%).

New Journal of Chemistry

A highly enantioselective Michael reaction between α,β-unsaturated ketones and malonic acid half-thioesters†

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A highly enantioselective Michael reaction between α,β-unsaturated ketones and malonic acid half-thioesters

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