Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones

被引:0
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作者
Ke Zhang [1 ,2 ,3 ]
Sheng Zuo [2 ,3 ]
Pengyuan You [2 ,3 ]
Tong Ru [2 ,3 ]
FenEr Chen [1 ,4 ,2 ,3 ]
机构
[1] Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, College of Pharmacy, Yanbian University
[2] Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University
[3] Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs
[4] College of Chemistry and Chemical Engineering, Jiangxi Normal
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O621.251 [];
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摘要
A novel asymmetric [4 + 2] cycloaddition of 2-methylidenetrimethylene carbonate with pyrrolidonederived enones has been achieved to produce the functionalized tetrahydropyran-fused spirocyclic scaffolds via palladium-catalysis. An array of enantioenriched spiro-pyrrolidine-2,3-diones bearing adjacent quaternary and tertiary stereocenters are obtained in high yields with excellent enantioselectivities(up to 96% yield and 99% ee). The further transformation of the product has been accomplished for the construction of medical interesting β2,2-amino acids and β-lactams. Preliminary mechanistic research was well conducted.
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页码:305 / 308
页数:4
相关论文
共 4 条
  • [1] Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones
    Ke Zhang
    Sheng Zuo
    Pengyuan You
    Tong Ru
    FenEr Chen
    Chinese Chemical Letters, 2024, 35 (06) : 305 - 308
  • [2] Palladium-catalyzed stereoselective decarboxylative [4+2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones
    Zhang, Ke
    Zuo, Sheng
    You, Pengyuan
    Ru, Tong
    Chen, Fen-Er
    CHINESE CHEMICAL LETTERS, 2024, 35 (06)
  • [3] Palladium-Catalyzed Asymmetric [4+2] Cycloaddition of 2-Methylidenetrimethylene Carbonate with Alkenes: Access to Chiral Tetrahydropyran-Fused Spirocyclic Scaffolds
    Mao, Biming
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    Xu, Yi
    Xu, Jiaqing
    Wang, Wei
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    Advanced Materials, 2020, 59 (28) : 11412 - 11416
  • [4] Palladium-Catalyzed Asymmetric [4+2] Cycloaddition of 2-Methylidenetrimethylene Carbonate with Alkenes: Access to Chiral Tetrahydropyran-Fused Spirocyclic Scaffolds
    Mao, Biming
    Liu, Honglei
    Yan, Zhengyang
    Xu, Yi
    Xu, Jiaqing
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    Wu, Yongjun
    Guo, Hongchao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11316 - 11320