Issue 13, 2013
From the journal:

Chemical Communications

3-Bromooxindoles as nucleophiles in asymmetric organocatalytic Mannich reactions with N-Ts-imines†

Jianhao Li,a   Taiping Du,a   Gang Zhang*a  and  Yungui Peng*a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Southwest University, 2 N. Tiansheng Road, Chongqing, P. R. China
E-mail: pengyungui@hotmail.com
Fax: +86 23-68253157
Tel: +86 23-68253157

Abstract

A direct asymmetric Mannich reaction of N-unprotected 3-bromooxindoles with N-Ts-imines catalyzed by bifunctional thiourea derived from 2-substituted cinchona alkaloid was developed. Products with vicinal chiral tertiary and brominated quaternary stereogenic centers were achieved in excellent diastereo- and enantioselectivity (up to 99 : 1 dr, 99% ee).

Graphical abstract: 3-Bromooxindoles as nucleophiles in asymmetric organocatalytic Mannich reactions with N-Ts-imines

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Article information

DOI
https://doi.org/10.1039/C2CC38475B
Article type
Communication
Submitted
25 Nov 2012
Accepted
19 Dec 2012
First published
19 Dec 2012

Chem. Commun., 2013,49, 1330-1332

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3-Bromooxindoles as nucleophiles in asymmetric organocatalytic Mannich reactions with N-Ts-imines

J. Li, T. Du, G. Zhang and Y. Peng, Chem. Commun., 2013, 49, 1330 DOI: 10.1039/C2CC38475B

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