Issue 10, 2010
From the journal:

Chemical Communications

Highly enantioselective Michael addition of cyclopentanone with chalconesvia novel di-iminium mechanism†

Junfeng Wang,a   Xin Wang,a   Zemei Ge,*a   Tieming Chenga  and  Runtao Li*a  

* Corresponding authors

a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, 38 Xueyuan Road, Beijing, P. R. China
E-mail: Lirt@mail.bjmu.edu.cn, Zmge@bjmu.edu.cn
Fax: +86-10-82716956
Tel: +86-10-82801504

Abstract

The highly efficient asymmetric Michael addition reactions of cyclopentanone with chalcones were catalyzed by a simple and commercially available chiral 1,2-diaminocyclohexane-hexanedioic acid, and exhibited good yields (up to 92%) and excellent enantioselectivities (up to 99% ee). A new di-iminium mechanism for the reaction was proposed.

Graphical abstract: Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism

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Article information

DOI
https://doi.org/10.1039/B915852A
Article type
Communication
Submitted
03 Aug 2009
Accepted
25 Nov 2009
First published
12 Jan 2010

Chem. Commun., 2010,46, 1751-1753

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Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism

J. Wang, X. Wang, Z. Ge, T. Cheng and R. Li, Chem. Commun., 2010, 46, 1751 DOI: 10.1039/B915852A

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