Stereodivergent Olefination of Enantioenriched Boronic Esters.

ABSTRACT: A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

SUBMITTER: Armstrong RJ 

PROVIDER: S-EPMC5347846 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature