Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (−)-Oseltamivir

Authors

  • Dr. Jiang Weng,

    1. Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P. R. China), Fax: (+86) 20-3994-3048
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  • Yong-Bo Li,

    1. Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P. R. China), Fax: (+86) 20-3994-3048
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  • Rui-Bin Wang,

    1. Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P. R. China), Fax: (+86) 20-3994-3048
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  • Prof. Dr. Gui Lu

    Corresponding author
    1. Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P. R. China), Fax: (+86) 20-3994-3048
    2. Institute of Human Virology, Sun Yat-sen University, Guangzhou, 510080 (P. R. China)
    • Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006 (P. R. China), Fax: (+86) 20-3994-3048
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Abstract

Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction of aldehydes. The addition products were obtained in good yields and very good to excellent enantioselectivities. Moreover, a highly efficient, enantioselective, and simple synthesis of (−)-oseltamivir was accomplished in only five steps: two separate one-pot operations and one purification step. This procedural simplicity demonstrated the power of the organocatalytic asymmetric Michael reaction of nitroenamine acceptors with aldehydes.

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