Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary aminethiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters†

Li-Na Jia,ab   Jun Huang,ab   Lin Peng,a   Liang-Liang Wang,ab   Jian-Fei Bai,ab   Fang Tian,a   Guang-Yun He,a   Xiao-Ying Xu*a  and  Li-Xin Wang*a  

* Corresponding authors

a Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People’s Republic of China
E-mail: wlxioc@cioc.ac.cn, xuxy@cioc.ac.cn
Fax: +86-028-8525-5208

b Graduate University of Chinese Academy of Sciences, Beijing 10039, People's Republic of China

Abstract

Chiral bifunctional tertiary amine thiourea was applied to catalyze the asymmetric hydroxyamination of 3-subsituted oxindoles with nitrosobenzene to construct 3-amino-2-oxindoles with quaternary stereocenters in good yields (up to 91%) and enantioselectivities (up to 90% ee).

Graphical abstract: Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary amine thiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters

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Article information

DOI
https://doi.org/10.1039/C1OB06413D
Article type
Communication
Submitted
18 Aug 2011
Accepted
26 Sep 2011
First published
26 Sep 2011

Org. Biomol. Chem., 2012,10, 236-239

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Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary amine thiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters

L. Jia, J. Huang, L. Peng, L. Wang, J. Bai, F. Tian, G. He, X. Xu and L. Wang, Org. Biomol. Chem., 2012, 10, 236 DOI: 10.1039/C1OB06413D

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