Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes

Lin-Wen Wei; Zhan-Cai Ma; Zhao-Qing Wang; Yu Zhao; Yuan Huang

doi:10.1055/a-2152-0355

Synthesis, Table of Contents

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

paper

Cobalt-Catalyzed Enantioselective Alkynylation of Oxabicyclic Alkenes

Lin-Wen Wei

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

,

Zhan-Cai Ma

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

,

Zhao-Qing Wang

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

,

Yu Zhao∗

^bDepartment of Chemistry, National University of Singapore, Singapore 117543, Singapore

,

Yuan Huang ∗

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

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Abstract

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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.

Key words

cobalt catalysis - ring-opening - alkynylation - desymmetrization - oxabicyclic alkenes

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References

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