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

original image

Hoch selektiv: Bei der Umwandlung von Pyrazolin-5-onen in 4-Oxo-4-arylbutenoate konnte die Enantioselektivität einer asymmetrischen Michael-Addition erstmals über das Metallzentrum des Katalysators geschaltet werden. Derselbe N,N′-Dioxid-Ligand L ergab mit verschiedenen Metallen die gezeigten Enantiomere von zahlreichen 4-substituierten 5-Pyrazolon-Derivaten. Tf=Trifluormethansulfonyl.

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