Litcius/Paper detail

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

Weiyuan Ma, Guanyu Han, Shaolin Kang, Xiaobo Pang, Xue‐Yuan Liu, Xing‐Zhong Shu

2021Journal of the American Chemical Society93 citationsDOI

Abstract

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 1,4-dienes. 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.

Topics & Concepts

ChemistryAllylic rearrangementElectrophileChemoselectivityCatalysisCobaltCombinatorial chemistryEnantioselective synthesisNickelOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms