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

14 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
Externally publishedYes

Fingerprint

Imines
Phosphoric acid
Amines
Hydrogen
Quinolines
Derivatives
Aromatization
Kinetics
Enantioselectivity
Acids
phosphoric acid
1,2,3,4-tetrahydroquinoline

ASJC Scopus subject areas

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

Cite this

Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines. / Saito, Kodai; Miyashita, Hiromitsu; Akiyama, Takahiko.

In: Chemical Communications, Vol. 51, No. 93, 2015, p. 16648-16651.

Research output: Contribution to journalArticle

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