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

Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes

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
› Author Affiliations
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).


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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