Issue 78, 2013
From the journal:

Chemical Communications

Cinchona-based squaramide-catalysed cascade aza-Michael–Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines†

Wen Yanga  and  Da-Ming Du*a  

* Corresponding authors

a School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
E-mail: dudm@bit.edu.cn
Tel: +86-10-68914985

Abstract

An efficient enantioselective cascade aza-Michael–Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25 : 1 dr) and high enantioselectivities (up to 94% ee).

Graphical abstract: Cinchona-based squaramide-catalysed cascade aza-Michael–Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines

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Article information

DOI
https://doi.org/10.1039/C3CC44930K
Article type
Communication
Submitted
01 Jul 2013
Accepted
01 Aug 2013
First published
01 Aug 2013

Chem. Commun., 2013,49, 8842-8844

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Cinchona-based squaramide-catalysed cascade aza-Michael–Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines

W. Yang and D. Du, Chem. Commun., 2013, 49, 8842 DOI: 10.1039/C3CC44930K

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