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Asymmetric Carbonyl-Ene Reaction Catalyzed by Chiral N,N′-Dioxide-Nickel(II) Complex: Remarkably Broad Substrate Scope

Ke Zheng, Jian Shi, Xiaohua Liu and Xiaoming Feng*

*Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China, Email: xmfengscu.edu.ch

K. Zheng, J. Shi, X. Liu, X. Feng, J. Am. Chem. Soc., 2008, 130, 15770-15771.

DOI: 10.1021/ja808023y (free Supporting Information)


Abstract

A novel nickel(II)-N,N′-dioxide complex facilitated the asymmetric synthesis of biologically interesting α-hydroxy carbonyl compounds under mild conditions by a highly enantioselective carbonyl-ene reactions of glyoxal derivatives with various alkenes. Various aromatic, aliphatic, and heteroaromatic glyoxal derivatives, as well as glyoxylate, were tolerated.

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Key Words

Ene Reaction, Homoallylic Alcohols


ID: J48-Y2008-3460