Brønsted acid-enhanced copper-catalyzed atroposelective cycloisomerization to axially chiral arylquinolizones via dearomatization of pyridine

Xiao-Long Min, Xiu-Lian Zhang, Wenbin Yi () and Ying He ()
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Xiao-Long Min: Nanjing University of Science & Technology
Xiu-Lian Zhang: Nanjing University of Science & Technology
Wenbin Yi: Nanjing University of Science & Technology
Ying He: Nanjing University of Science & Technology

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract The construction of axially chiral N-heterobiaryls is of great interest as a result of their occurrence in organocatalysts, chiral ligands, natural products, and biologically active molecules. Despite remarkable achievements in this area, strategies for the preparation of new classes of axially chiral N-heterobiaryls remain to be further explored. Herein, we report the enantioselective synthesis of axially chiral arylquinolizones through an intramolecular atroposelective cycloisomerization. The reaction proceeds via the Brønsted acid-enhanced dearomatization of pyridine by a copper catalyst that allows for the formation of the desired products in excellent yields and enantioselectivities. The utility of this methodology is illustrated by a synthesis on gram scale production and transformation of the products into chiral thiourea catalysts. Mechanistic studies demonstrate that Brønsted acid plays a significant role in promoting the reactivity of the reaction, while both the steric and electronic effects of aryl substituents in substrate play a role in controlling the stereoselectivity.

Date: 2022
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DOI: 10.1038/s41467-022-27989-3

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