Issue 13, 2011
From the journal:

Chemical Communications

Efficient synthesis of optically active 4-nitro-cyclohexanonesvia bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones†

Bin Wu,a   Guo-Gui Liu,a   Mei-Qiu Li,a   Yong Zhang,a   Shao-Yun Zhang,a   Jun-Ru Qiu,a   Xiao-Ping Xu,a   Shun-Jun Ji*a  and  Xing-Wang Wang*a  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
E-mail: wangxw@suda.edu.cn

Abstract

Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 ∶ 1) and high enantiomeric ratios (up to 97 ∶ 3).

Graphical abstract: Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

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Article information

DOI
https://doi.org/10.1039/C0CC05418F
Article type
Communication
Submitted
07 Dec 2010
Accepted
20 Jan 2011
First published
17 Feb 2011

Chem. Commun., 2011,47, 3992-3994

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Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

B. Wu, G. Liu, M. Li, Y. Zhang, S. Zhang, J. Qiu, X. Xu, S. Ji and X. Wang, Chem. Commun., 2011, 47, 3992 DOI: 10.1039/C0CC05418F

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