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Facile and Efficient Enantioselective Hydroxyamination Reaction: Synthesis of 3-Hydroxyamino-2-Oxindoles Using Nitrosoarenes

Authors

  • Ke Shen,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
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  • Dr. Xiaohua Liu,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
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  • Gang Wang,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
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  • Dr. Lili Lin,

    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
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  • Prof. Dr. Xiaoming Feng

    Corresponding author
    1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
    • Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China), Fax: (+86)28-8541-8249
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  • We acknowledge the National Natural Science Foundation of China (Nos. 2073 2003 and 21021001 and 20872096) and the National Basic Research Program of China (973 Program: No. 2010CB833300) for financial support, and Sichuan University Analytical & Testing Centre for NMR analysis.

Abstract

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Sc takes action: The highly enantioselective hydroxyamination reaction of N-unprotected 2-oxindoles with nitrosoarenes has been realized using the Sc(OTf)3/L1 complex. The catalyst system exhibited remarkably broad substrate scope and high efficiency. This transformation is the first example of a chiral ScIII/enolate activating a nitrosoarene, and can be conducted on a gram scale without loss in the ee values.

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