Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea†

Xin Li,*a   Xiao-Song Xue,‡a   Cong Liu,‡a   Bin Wang,b   Bo-Xuan Tan,a   Jia-Lu Jin,a   Yue-Yan Zhang,a   Nan Donga  and  Jin-Pei Cheng*a  

* Corresponding authors

a State Key Laboratory of Elemento-organic Chemistry and Department of Chemistry, Nankai University, Tianjin, China
E-mail: xin_li@nankai.edu.cn
Fax: (+86)-22-23499147
Tel: (+86)-22-23499174

b Tianjin Key Laboratory of Structure and Performance for Functional Molecule, College of Chemistry, Tianjin Normal University, Tianjin, China

Abstract

The current work reports an organocatalytic strategy for the asymmetric catalysis of chiral benzofuran-2(3H)-ones bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of nitroolefins and 3-substituted benzofuran-2(3H)-ones to give the desired chiral benzofuran-2(3H)-one products with moderate to excellent yields (up to 98%) and moderate to very good selectivities (up to 19 : 1 dr and up to 91% ee). Theoretical calculations using the DFT method on the origin of the stereoselectivity were conducted. The effect of the nitroolefin substituent position on the stereoselectivity of the Michael addition reaction was also theoretically rationalized.

Graphical abstract: Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea

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Article information

DOI
https://doi.org/10.1039/C1OB06518A
Article type
Paper
Submitted
04 Sep 2011
Accepted
29 Sep 2011
First published
30 Sep 2011

Org. Biomol. Chem., 2012,10, 413-420

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Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea

X. Li, X. Xue, C. Liu, B. Wang, B. Tan, J. Jin, Y. Zhang, N. Dong and J. Cheng, Org. Biomol. Chem., 2012, 10, 413 DOI: 10.1039/C1OB06518A

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