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Catalytic Asymmetric [4+2] Annulation Initiated by an Aza-Rauhut–Currier Reaction: Facile Entry to Highly Functionalized Tetrahydropyridines

Authors

  • Zugui Shi,

    1. College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, 16 Xue-Lin Street, Hangzhou 310036, Zhejiang (China)
    2. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Peiyuan Yu,

    1. College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, 16 Xue-Lin Street, Hangzhou 310036, Zhejiang (China)
    2. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Prof. Dr. Teck-Peng Loh,

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
    2. Department of Chemistry, University of Sciences and Technology of China, Hefei 230026, Anhui (China)
    • Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
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  • Prof. Dr. Guofu Zhong

    Corresponding author
    1. College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, 16 Xue-Lin Street, Hangzhou 310036, Zhejiang (China)
    2. Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore)
    • College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, 16 Xue-Lin Street, Hangzhou 310036, Zhejiang (China)
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  • Research support from the Hangzhou Normal University (China) is gratefully acknowledged. We thank Dr. Y.-X. Li for the X-ray crystallographic analysis.

Abstract

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Under control: The first example of chiral amino phosphine catalysts for the title reaction between vinyl ketones and N-sulfonyl-1-aza-1,3-dienes has been developed. Under ambient conditions, this protocol provides straightforward access to densely functionalized, enantioenriched tetrahydropyridines with high levels of sterecontrol in good to excellent yields.

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