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Catalytic Asymmetric β,γ Activation of α,β-Unsaturated γ-Butyrolactams: Direct Approach to β,γ-Functionalized Dihydropyranopyrrolidin-2-ones

Authors

  • Dr. Xianxing Jiang,

    Corresponding author
    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)
    • Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)

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    • These authors contributed equally to this work.

  • Luping Liu,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)
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    • These authors contributed equally to this work.

  • Panpan Zhang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)
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  • Yuan Zhong,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)
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  • Prof. Dr. Rui Wang

    Corresponding author
    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)
    • Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Institute of Biochemistry and Molecular Biology, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000 (China)

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  • We are grateful for the grants from the National Natural Science Foundation of China (Nos. 90813012, 20932003, and 21202072), the Key National S&T Program “Major New Drug Development” of the Ministry of Science and Technology of China (2012ZX09504-001-003).

Abstract

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Skeleton in the closet: The title reaction enables the development of the first catalytic β,γ-selective Diels–Alder [4+2] annulation of α,β-unsaturated γ-butyrolactams (see scheme; Boc=tert-butoxycarbonyl, Ts=4-toluenesulfonyl). This process provides a direct method for the enantioselective construction of bi- or tricyclic dihydropyranopyrrolidin-2-one skeletons in only one step.

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