Chiral Phosphoric Acid Catalyzed Kinetic Resolution of Indolines Based on a Self-Redox Reaction

Kodai Saito, Takahiko Akiyama

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17 Citations (Scopus)

Abstract

A strategy for oxidative kinetic resolution of racemic indolines was developed, employing salicylaldehyde derivative as the pre-resolving reagent and chiral phosphoric acid as the catalyst. The iminium intermediate, formed by the condensation reaction of an enantiomer of indoline with salicylaldehyde derivative, was hydrogenated by the same enantiomer of indoline to afford another enantiomer of indoline by a self-redox mechanism. The oxidative kinetic resolution of 2-aryl-substituted indolines proceeded to give enantiomers in good yields with excellent enantioselectivities.

Original languageEnglish
Pages (from-to)3148-3152
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number9
DOIs
Publication statusPublished - 2016 Feb 24

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Keywords

  • asymmetric synthesis
  • heterocycles
  • hydrogen transfer
  • kinetic resolution
  • organocatalyst

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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