Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Nitrones to Alkylidene Malonates: Highly Enantioselective Synthesis of Multisubstituted Isoxazolidines

Authors

  • Donghui Chen,

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

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

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

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All under control! A catalytic asymmetric 1,3-dipolar cycloaddition reaction of nitrones to alkylidene malonates, catalyzed by chiral N,N′-dioxide–Ni(ClO4)26 H2O complexes, has been developed with excellent yields, diastereo-, and enantioselectivities (see scheme, R1=aryl, R2=alkyl, R3, R4=Ph). In addition, a possible transition state has also been proposed to elucidate the high level of enantio- and diastereocontrol.

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