Issue 10, 2011
From the journal:

Chemical Science

Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins†

Miao Ding,a   Feng Zhou,a   Yun-Lin Liu,a   Cui-Hong Wang,a   Xiao-Li Zhaoa  and  Jian Zhou*a  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, China
E-mail: jzhou@chem.ecnu.edu.cn
Fax: (+86) 21-6223-4560

Abstract

A newly developed cinchonidine-derived phosphoramide 6b, simple and easily available, was identified as a powerful catalyst for the highly enantioselective Michael addition of both unprotected 3-aryl and 3-alkyloxindoles to β-substituted nitroalkenes to furnish the C3 quaternary stereogenic carbon center with an adjacent tertiary stereocenter in up to 21 : 1 diastereoselectivity and up to 99% enantioselectivity.

Graphical abstract: Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

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Article information

DOI
https://doi.org/10.1039/C1SC00390A
Article type
Edge Article
Submitted
24 Jun 2011
Accepted
12 Jul 2011
First published
03 Aug 2011

Chem. Sci., 2011,2, 2035-2039

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Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins

M. Ding, F. Zhou, Y. Liu, C. Wang, X. Zhao and J. Zhou, Chem. Sci., 2011, 2, 2035 DOI: 10.1039/C1SC00390A

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