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Bifunctional Cinchona Alkaloid Thiourea Catalyzed Highly Efficient, Enantioselective Aza-Henry Reaction of Cyclic Trifluoromethyl Ketimines: Synthesis of Anti-HIV Drug DPC 083

Authors

  • Dr. Hexin Xie,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
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  • Dr. Yinan Zhang,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
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  • Dr. Shilei Zhang,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
    2. School of Pharmacy, East China University of Science & Technology, 130 Mei-Long Road, Shanghai 200237 (China)
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  • Xiaobei Chen,

    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
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  • Prof. Dr. Wei Wang

    Corresponding author
    1. Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
    2. School of Pharmacy, East China University of Science & Technology, 130 Mei-Long Road, Shanghai 200237 (China)
    • Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001 (USA)
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  • Financial support of this research provided by the National Science foundation (CHE-1057569), the China 111 Project (Grant B07023), and the East China University of Science & Technology is gratefully acknowledged.

Abstract

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Highly efficient: The title reaction provides biologically interesting chiral trifluoromethyl dihydroquinazolinone frameworks in high yields (up to 97 %) and with high enantioselectivities (up to 98 % ee), using as low as 1 mol % of catalyst (see scheme). Moreover, anti-HIV drug candidate DPC 083 was efficiently synthesized using the highly enantioselective aza-Henry reaction as a key step.

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