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

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

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.

Organic & biomolecular chemistry 2012 Jan 14

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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).

Citation

Li-Na Jia, Jun Huang, Lin Peng, Liang-Liang Wang, Jian-Fei Bai, Fang Tian, Guang-Yun He, Xiao-Ying Xu, Li-Xin Wang. Asymmetric hydroxyamination of oxindoles catalyzed by chiral bifunctional tertiary amine thiourea: construction of 3-amino-2-oxindoles with quaternary stereocenters. Organic & biomolecular chemistry. 2012 Jan 14;10(2):236-9