Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

Brian P. Woods, Manuel Orlandi, Chung Yang Huang, Matthew S. Sigman, Abigail G. Doyle

Research output: Contribution to journalArticle

81 Scopus citations

Abstract

A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

Original languageEnglish (US)
Pages (from-to)5688-5691
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number16
DOIs
StatePublished - Apr 26 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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