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Highly Enantioselective Direct Michael Addition of Nitroalkanes to Nitroolefins Catalyzed by La(OTf)3/N,N′-Dioxide Complexes

Authors

  • Xu 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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  • Xin Zhou,

    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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  • 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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  • Lu Chang,

    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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  • Xiaohua Liu Dr.,

    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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  • Xiaoming Feng Prof. Dr.

    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
    2. State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041 (P. R. China)
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  • We thank the National Natural Science Foundation of China (No. 20732003) and the Ministry of Education (No. 20070610019) for financial support. We also thank Sichuan University Analytical & Testing Center for NMR analysis, and the State Key Laboratory of Biotherapy for HRMS analysis.

Abstract

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It all adds up: A chiral La(OTf)3/N,N′-dioxide complex has been developed for the asymmetric direct Michael addition of nitroalkanes to nitroalkenes. This reaction afford 1,3-dinitro compounds with two stereocenters in good yields with high diastereo- and enantioselectivity (up to d.r. 93:3, 97 % ee; see scheme, Tf=trifluoromethanesulfonyl) under mild conditions.

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