Synthesis 2023; 55(23): 3954-3960
DOI: 10.1055/a-2152-0355
paper

Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes

Authors

  • Lin-Wen Wei

    a   Department of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, P. R. of China
  • Zhan-Cai Ma

    a   Department of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, P. R. of China
  • Zhao-Qing Wang

    a   Department of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, P. R. of China
  • Yu Zhao

    b   Department of Chemistry, National University of Singapore, Singapore 117543, Singapore
  • Yuan Huang

    a   Department of Medicinal Chemistry, School of Pharmacy, Xi’an Jiaotong University, Xi’an 710061, P. R. of China

We are grateful for the financial support from the National Natural Science Foundation of China (No.22001203), the Ministry of Education - Singapore (A-8000055-00-00), and the Faculty of Science, National University of Singapore (A-8001040-00-00).


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Abstract

Efficient access to enantioenriched cyclic homopropargylic alcohols through an unprecedented cobalt-catalyzed asymmetric alkynylation of oxabicyclic alkenes has been developed. By using inexpensive cobalt salt/chiral bisphosphine ligand as the catalyst and easy-to-handle potassium alkynyltrifluoroborates as the nucleophile, synthetically valuable homopropargylic alcohols are obtained in moderate to good yields and high enantioselectivities.

Supporting Information



Publication History

Received: 07 July 2023

Accepted after revision: 10 August 2023

Accepted Manuscript online:
10 August 2023

Article published online:
22 September 2023

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