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Issue 52, 2018
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A one-pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination (ARA)

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Abstract

Asymmetric reductive amination for the synthesis of both chiral tetrahydroquinolines (THQs) and tetrahydroisoquinolines (THIQs) has been realized with an Ir/ZhaoPhos catalytic system via a one-pot N-Boc deprotection/intramolecular asymmetric reductive amination (ARA) sequence. Control experiments reveal that HCl plays a vital role to the success of this transformation. The HCl acid assists the removal of the N-Boc protecting group and also provides chloride ions to interact with the thiourea moiety in ZhaoPhos, thus leading to excellent reaction enantiocontrol.

Graphical abstract: A one-pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination (ARA)

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Publication details

The article was received on 04 May 2018, accepted on 29 May 2018 and first published on 06 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC03586E
Citation: Chem. Commun., 2018,54, 7247-7250
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    A one-pot process for the enantioselective synthesis of tetrahydroquinolines and tetrahydroisoquinolines via asymmetric reductive amination (ARA)

    T. Yang, Q. Yin, G. Gu and X. Zhang, Chem. Commun., 2018, 54, 7247
    DOI: 10.1039/C8CC03586E

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