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

Jianhao Li; Taiping Du; Gang Zhang; Yungui Peng

doi:10.1039/C2CC38475B

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Chemical Communications

Issue 13, 2013

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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

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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

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

DOI: 10.1039/C2CC38475B
Received 25 Nov 2012, Accepted 19 Dec 2012
First published online 19 Dec 2012

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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).