4.8 Article

Cobalt-Catalyzed Enantiospecific Dynamic Kinetic Cross-Electrophile Vinylation of Allylic Alcohols with Vinyl Triflates

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 39, Pages 15930-15935

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c08695

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Funding

  1. National Natural Science Foundation of China [21772072, 22071084]

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The study presents a new method for synthesizing enantioenriched 1,4-dienes using cobalt catalysis, demonstrating high enantiospecificity and chemoselectivity.
Asymmetric cross-electrophile coupling has emerged as a promising tool for producing chiral molecules; however, the potential of this chemistry with metals other than nickel remains unknown. Herein, we report a cobalt-catalyzed enantiospecific vinylation reaction of allylic alcohol with vinyl triflates. This work establishes a new method for the synthesis of enantioenriched 1,4dienes. The reaction proceeds through a dynamic kinetic coupling approach, which not only allows for direct functionalization of allylic alcohols but also is essential to achieve high chemoselectivity. The use of cobalt enables the reactions to proceed with high enantiospecificity, which have failed to be realized by nickel catalysts.

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