Catalytic Atroposelective Synthesis of N-Aryl Quinoid Compounds.
J Am Chem Soc
; 142(5): 2198-2203, 2020 02 05.
Article
em En
| MEDLINE
| ID: mdl-31944689
ABSTRACT
Diarylamines and related scaffolds are among the most common chemotypes in modern drug discovery. While they can potentially possess two chiral axes, there are no studies on their enantioselective synthesis, as these axes typically possess lower stereochemical stabilities. Herein, we report a chiral phosphoric acid catalyzed atroposelective electrophilic halogenation of N-aryl quinoids, a class of compounds that are analogous to diarylamines. This chemistry yields a large range of stereochemically stable N-aryl quinoids in excellent yields and atroposelectivity. This work represents the first example of the atroposelective synthesis of a diarylamine-like scaffold and will serve as a gateway to fundamental and applied studies on the scarcely studied chirality of these ubiquitous chiral scaffolds.
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Base de dados:
MEDLINE
Assunto principal:
Hidroquinonas
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article