Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via SNAr

Mariel M. Cardenas; Mirza A. Saputra; Deane A. Gordon; Andrea N. Sanchez; Nobuyuki Yamamoto; Jeffrey L. Gustafson

doi:10.1039/D1CC04335H

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Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via S_NAr†

Mariel M. Cardenas,^a Mirza A. Saputra,^a Deane A. Gordon,^a Andrea N. Sanchez,^a Nobuyuki Yamamoto^a and Jeffrey L. Gustafson

*^a

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* Corresponding authors

^a College of Sciences, Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, California, USA
E-mail: JGustafson@sdsu.edu

Abstract

Herein we report the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines via the nucleophilic aromatic substitution (S_NAr) of thiophenols into 3-aryl-2-fluoroquinolines mediated by catalytic amounts of Cinchona alkaloid-derived ureas. These reactions displayed a spectrum of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characters depending upon the stereochemical stability of the starting material. Low barrier substrates proceeded via DKR while higher barrier substrates proceeded via KR. On the other hand, substrates with intermediate stabilities displayed hallmarks of both DKR and KR. Finally, we also show that we can functionalize the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds with minimal observed racemization.

This article is part of the themed collection: 2021 Emerging Investigators

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Article information

DOI: https://doi.org/10.1039/D1CC04335H
Article type: Communication
Submitted: 10 Aug 2021
Accepted: 06 Sep 2021
First published: 06 Sep 2021

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Chem. Commun., 2021,57, 10087-10090

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Catalytic atroposelective dynamic kinetic resolutions and kinetic resolutions towards 3-arylquinolines via S_NAr

M. M. Cardenas, M. A. Saputra, D. A. Gordon, A. N. Sanchez, N. Yamamoto and J. L. Gustafson, Chem. Commun., 2021, 57, 10087 DOI: 10.1039/D1CC04335H

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