Synthesis 2006(22): 3795-3800  
DOI: 10.1055/s-2006-950339
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Effective Bifunctional Thiourea Catalyst for Highly Enantio- and Diastereoselective Michael Addition of Cyclohexanone to Nitroolefins

Yi-Ju Cao, Hai-Hua Lu, Yuan-Yuan Lai, Liang-Qiu Lu, Wen-Jing Xiao*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. of China
Fax: +86(27)67862041; e-Mail: wxiao@mail.ccnu.edu.cn;
Further Information

Publication History

Received 5 September 2006
Publication Date:
02 November 2006 (eFirst)

Abstract

A series of new tunable and bifunctional thiourea catalysts have been synthesized and their catalytic activities are evaluated in the direct Michael addition of cyclohexanone to nitroolefins. High isolated yields (up to 97%), enantioselectivities (up to 98%) and diastereoselectivities (up to 99:1) were obtained under the optimal conditions.

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8

The reaction proceeded slowly, and there were only trace amounts of products formed even after seven days.