Highly Enantioselective Michael Addition of Pyrazolin-5-ones Catalyzed by Chiral Metal/N,N′-Dioxide Complexes: Metal-Directed Switch in Enantioselectivity

Authors

  • Zhen 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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  • Zhigang Yang,

    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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  • Donghui Chen,

    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 acknowledge the National Natural Science Foundation of China (Nos. 20732003 and 21021001), the PCSIRT (No. IRT0846), and the National Basic Research Program of China (973 Program: No. 2011CB808600) for financial support. We also thank the Sichuan University Analytical & Testing Center for NMR analysis.

Abstract

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Make the switch: The first example of a switch in enantioselectivity in the asymmetric Michael addition of pyrazolin-5-ones to 4-oxo-4-arylbutenoates that is controlled by the metal center of the catalyst is reported. By using the same N,N′-dioxide ligand L with different metals the respective enantiomers of various 4-substituted 5-pyrazolone derivatives were obtained. Tf=trifluoromethanesulfonyl.

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