Enantioselective catalytic 1,2-boronate rearrangements.

ABSTRACT: A strategy that facilitates the construction of a wide variety of trisubstituted stereocenters through a catalytically accessed common chiral intermediate could prove highly enabling for the field of synthetic chemistry. We report the discovery of enantioselective, catalytic 1,2-boronate rearrangements for the synthesis of α-chloro pinacol boronic esters from readily available boronic esters and dichloromethane. The chiral building blocks produced in these reactions can undergo two sequential stereospecific elaborations to generate a wide assortment of trisubstituted stereocenters. The enantioselective reaction is catalyzed by a lithium-isothiourea-boronate complex, which is proposed to promote rearrangement through a dual–lithium-induced chloride abstraction orchestrated by Lewis basic fu

SUBMITTER: Sharma HA 

PROVIDER: S-EPMC8591546 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature