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Issue 93, 2015
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Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

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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.

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

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Supplementary files

Article information


Submitted
31 Jul 2015
Accepted
15 Sep 2015
First published
21 Sep 2015

Chem. Commun., 2015,51, 16648-16651
Article type
Communication

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

K. Saito, H. Miyashita and T. Akiyama, Chem. Commun., 2015, 51, 16648
DOI: 10.1039/C5CC06436H

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