Cobalt-Catalyzed Enantioselective Dicarbofunctionalization of Acrylates

Abstract

Catalytic enantioselective alkene difunctionalization represents a powerful tool for the rapid assembly of complex chiral molecules and has found wide range of applications in synthetic chemistry. Enantioselective control of the newly formed pro-chiral carbon centers using chiral cobalt catalyst, however, remains challenging. Herein, we report the first cobalt-catalyzed enantioselective difunctionalization of industry-relevant acrylates with lithium aryl boronates and α,α-dialkyl bromoacetate for the preparation of enantioenriched glutaric acid derivatives. Facile transformations of the resulting α-aryl esters to other functionalities have been achieved. To further showcase the synthetic utility of the current protocol, application to the enantioselective synthesis of an analog of (−)-preclamol was demonstrated.