Europe PMC N-Sulfonyl Imines: Highly Enantio- and Diastereoselective Construction of Chiral Tetrahydrofuran Scaffolds Bearing Three Vicinal and Quaternary Stereocenters.">N-Sulfonyl Imines: Highly Enantio- and Diastereoselective Construction of Chiral Tetrahydrofuran Scaffolds Bearing Three Vicinal and Quaternary Stereocenters.">
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Palladium-Catalyzed Asymmetric [3 + 2] Annulation of Vinylethylene Carbonates with Alkenes Installed on Cyclic N-Sulfonyl Imines: Highly Enantio- and Diastereoselective Construction of Chiral Tetrahydrofuran Scaffolds Bearing Three Vicinal and Quaternary Stereocenters.

Author information

Affiliations

  • 1. Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
      Authors
    • Ke M 1
    • Yu Y 1
    • Li X 1
    • Xiao X 1
    • Chen F 1
    (5 authors)
  • 2. Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.
      Authors
    • Qiao B 2
    • Li SJ 2
    • Lan Y 2
    (3 authors)

ORCIDs linked to this article

The Journal of Organic Chemistry, 04 Apr 2022, 87(8):5166-5177
https://doi.org/10.1021/acs.joc.1c03157 PMID: 35377155 

Abstract 

A multisubstituted tetrahydrofuran building block bearing three vicinal chiral carbon centers widely exists in a broad spectrum of bioactive natural products, and the development of efficient and convenient methods to establish this skeleton remains a challenging task. Herein, we have developed an efficient method for the construction of significant tetrahydrofuran scaffolds bearing three vicinal and α-quaternary chiral carbon stereocenters through Pd-catalyzed asymmetric [3 + 2] annulation of vinylethylene carbonates with alkenes installed on cyclic N-sulfonyl imines. A series of multisubstituted tetrahydrofuran derivatives are obtained in high efficiencies with excellent enantioselectivities and diastereoselectivities. Density functional theory (DFT) studies are accomplished to rationalize the stereocontrol of the annulation process and disclose that methanol could be applied to stabilize the reactive zwitterionic π-allylpalladium via the H-bond interaction.

Full text links 

Read article at publisher's site: https://doi.org/10.1021/acs.joc.1c03157

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Funding 

Funders who supported this work.

National Natural Science Foundation of China (1)

Natural Science Foundation of Zhejiang Province (1)