Catalytic Asymmetric Addition of Alkyl Enol Ethers to 1,2-Dicarbonyl Compounds: Highly Enantioselective Synthesis of Substituted 3-Alkyl-3-Hydroxyoxindoles

Authors

  • Ke Zheng,

    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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  • Chengkai Yin,

    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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  • 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 appreciate the financial support from the National Natural Science Foundation of China (Nos. 20732003 and 21021001 and 20872096) and the National Basic Research Program of China (973 Program: No. 2010CB833300). We thank the Sichuan University Analytical & Testing Centre for NMR and X-ray diffraction analysis.

Abstract

original image

A familiar ring: An efficient catalytic asymmetric hetero-ene reaction of 1,2-dicarbonyl compounds (including isatins, α-ketoesters, and glyoxal derivatives) is described. The catalyst system derived from 1 can be used for a broad substrate scope and the corresponding products were obtained in good yield and excellent enantioselectivity. M.S.=molecular sieves.

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