Stereodivergent Olefination of Enantioenriched Boronic Esters

Roly J. Armstrong, Cristina García-Ruiz, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

34 Citations (Scopus)
251 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)786-790
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number3
Early online date13 Dec 2016
DOIs
Publication statusPublished - 16 Jan 2017

Keywords

  • alkenes
  • boron
  • isomers
  • oxidation
  • selenium

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