Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A chiral Brønsted acid catalyzed dehydrogenative kinetic resolution of tetrahydroquinoline derivatives, which are representative of cyclic secondary amines, based on their hydrogen transfer to aromatic imines was efficiently achieved with high enantioselectivities. This hydrogen transfer of tetrahydroquinolines to imines was not driven by their aromatization to quinolines. This dehydrogenative kinetic resolution could be also applied to the asymmetric synthesis of various benzofused heterocycles containing secondary amine cores.

Original languageEnglish
Pages (from-to)16648-16651
Number of pages4
JournalChemical Communications
Volume51
Issue number93
DOIs
Publication statusPublished - 2015 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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