title: 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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Roly J
authors.initials: RJ
authors.lastname: Armstrong
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Cristina
authors.initials: C
authors.lastname: García-Ruiz
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Eddie L
authors.initials: EL
authors.lastname: Myers
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
authors.forename: Varinder K
authors.identifier: 0000-0003-0344-6430
authors.initials: VK
authors.lastname: Aggarwal
keywords: alkenes; boron; isomers; oxidation; selenium