Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides

Erin E. Stache, Tomislav Rovis, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

The enantioselective desymmetrization of cyclic meso-anhydrides with benzyl trifluoroborates under nickel-photoredox catalysis is described. The reaction tolerates a variety of sterically and electronically different trifluoroborates, as well as structurally unique cyclic anhydrides. The trans isomer of the keto-acid products is also observed at varying levels dependent on the trifluoroborate identity and relative catalyst loading. A mechanism involving decarbonylation and Ni−C bond homolysis of a NiII adduct is proposed. This feature allows access to a trans keto-acid as the major product in high enantioselectivity from a cis meso anhydride.

Original languageEnglish (US)
Pages (from-to)3679-3683
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number13
DOIs
StatePublished - 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • asymmetric synthesis
  • cross-coupling
  • desymmetrization
  • nickel
  • photoredox catalysis

Fingerprint Dive into the research topics of 'Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides'. Together they form a unique fingerprint.

Cite this