Synlett 2024; 35(18): 2101-2106
DOI: 10.1055/a-2290-0894
letter

Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reaction of Vinyl Cyclopropane with Electron-Deficient Dienes

Authors

  • Yun-Fan Li

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
  • Cun Yang

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
  • Yu-Ting Xi

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
  • Qitao Tan

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
  • Chang-Hua Ding

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
  • Bin Xu

    a   Department of Chemistry, Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
    b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

We thank the National Natural Science Foundation of China (No. 22071143, 22171178, 21971159) and Innovation Program of the Shanghai Municipal Education Commission (No. 2019-01-07-00-09-E00008) for financial support.


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Abstract

Palladium-catalyzed asymmetric [3+2] cycloaddition reaction of vinyl cyclopropane and electron-deficient dienes was realized. The cycloaddition reaction proceeded regioselectively on the distant C=C double bond of electron-deficient dienes, and was mainly controlled by the steric hindrance of the 5-substituent of electron-deficient dienes. Chiral multi-substituted cyclopentanes bearing three functional groups (monosubstituted alkene, conjugated ester, and cyano) and three continuous stereocenters were obtained in moderate to high yields, diastereoselectivities, and enantioselectivities.

Supporting Information



Publikationsverlauf

Eingereicht: 06. Januar 2024

Angenommen nach Revision: 18. März 2024

Accepted Manuscript online:
18. März 2024

Artikel online veröffentlicht:
03. April 2024

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