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Catalytic Atroposelective Synthesis of

Catalytic Atroposelective Synthesis of

Authors :
Sagar D, Vaidya
Sean T, Toenjes
Nobuyuki, Yamamoto
Sean M, Maddox
Jeffrey L, Gustafson
Source :
J Am Chem Soc
Publication Year :
2020

Abstract

Diarylamines are among the most common chemotypes in modern drug discovery. While diarylamines can potentially possess two axes of chirality, there are no studies on their catalytic 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.

Details

ISSN :
15205126
Volume :
142
Issue :
5
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.pmid..........59991ba6e2c4dca1e25f61209b1f1c5e