Issue 38, 2013
From the journal:

Chemical Communications

A highly efficient access to enantiopure tetrahydropyridines: dual-organocatalyst-promoted asymmetric cascade reaction†

Hua Lin,a   Yu Tan,a   Wen-Jie Liu,a   Zhi-Cheng Zhang,a   Xing-Wen Sun*a  and  Guo-Qiang Lin*a  

* Corresponding authors

a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, P. R. China
E-mail: sunxingwen@fudan.edu.cn, lingq@sioc.ac.cn
Fax: +86 21 5566 4460
Tel: +86 21 5566 4460

Abstract

A highly efficient cascade process of Michael–aza-Henry–hemiaminalization–dehydration was established for the construction of enantiopure tetrahydropyridines using the combination of prolinol trimethylsilyl ether and cinchona alkaloid catalysts. This new approach allowed for the application of aliphatic imines, generated in situ from aldehydes and amines. Good yields (up to 90%), high enantio- (up to >99% ee) and diastereoselectivities (>99 : 1 d.r. in all cases) were achieved for a broad spectrum of substrates under mild conditions.

Graphical abstract: A highly efficient access to enantiopure tetrahydropyridines: dual-organocatalyst-promoted asymmetric cascade reaction

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Article information

DOI
https://doi.org/10.1039/C3CC40690C
Article type
Communication
Submitted
27 Jan 2013
Accepted
21 Mar 2013
First published
21 Mar 2013

Chem. Commun., 2013,49, 4024-4026

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A highly efficient access to enantiopure tetrahydropyridines: dual-organocatalyst-promoted asymmetric cascade reaction

H. Lin, Y. Tan, W. Liu, Z. Zhang, X. Sun and G. Lin, Chem. Commun., 2013, 49, 4024 DOI: 10.1039/C3CC40690C

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