Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels–Alder Reactions: Highly Efficient In Situ Substrate Generation and Activation to Construct Azaspirocyclic Skeletons

Authors

  • Dr. Xianxing Jiang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
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  • Xiaomei Shi,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
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  • Shoulei Wang,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
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  • Tao Sun,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
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  • Dr. Yiming Cao,

    1. Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, 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; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
    • Key Laboratory of Preclinical Study for New Drugs of Gansu Province; Institute of Biochemistry and Molecular Biology, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000 (China)
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  • We are grateful for the grants from the National Natural Science Foundation of China (nos. 20932003 and 90813012) and the Key National S&T Program “Major New Drug Development” of the Ministry of Science and Technology of China (2012ZX09504-001-003).

Abstract

original image

Skeletons in the flask: The first highly enantioselective organocatalytic version of the title reaction using an in situ substrate generation/activation catalytic mode is described (see scheme). The reaction provides an efficient enantioselective construction of functionalized azaspirocyclic skeletons. The in situ generation of the enolate provides a new way in which to use this important nucleophile in organic synthesis.

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