Issue 15, 2009
From the journal:

Organic & Biomolecular Chemistry

Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst†

Aidang Lu,a   Peng Gao,a   Yang Wu,a   Youming Wang,a   Zhenghong Zhou*a  and  Chuchi Tanga  

* Corresponding authors

a State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, P. R. China
E-mail: z.h.zhou@nankai.edu.cn
Fax: +86-22-23508939

Abstract

A novel bifunctional thiourea bearing a saccharide-scaffold and a secondary amino group was synthesized, and was proven to be an effective organocatalyst for the asymmetric Michael reaction of cyclohexanone to both aryl and alkyl nitroolefins. The corresponding adducts were obtained with excellent diastereo- (up to >99/1 dr) and enantioselectivities (up to 97% ee).

Graphical abstract: Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst

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Article information

DOI
https://doi.org/10.1039/B905306A
Article type
Paper
Submitted
19 Mar 2009
Accepted
07 May 2009
First published
11 Jun 2009

Org. Biomol. Chem., 2009,7, 3141-3147

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Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst

A. Lu, P. Gao, Y. Wu, Y. Wang, Z. Zhou and C. Tang, Org. Biomol. Chem., 2009, 7, 3141 DOI: 10.1039/B905306A

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