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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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Publication details

The article was received on 31 Jul 2015, accepted on 15 Sep 2015 and first published on 21 Sep 2015


Article type: Communication
DOI: 10.1039/C5CC06436H
Citation: Chem. Commun., 2015,51, 16648-16651
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    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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