Chiral Brønsted Acid-Catalyzed Kinetic Resolution of Sulfoximines for the Synthesis of Benzothiadiazine-1-Oxides.

J Org Chem

Key Laboratory of Chemical Biology and Traditional Chinese Medicine (Ministry of Educational of China), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. China.

Published: June 2024

Benzothiadiazine-1-oxide scaffolds with -stereogenic centers are prevalent in bioactive and pharmaceutical molecules. Reported works mainly focused on the metal-catalyzed asymmetric C-H amination/cyclization reaction for the synthesis of benzothiadiazine-1-oxides. Here, we reported a chiral phosphoric acid-catalyzed kinetic resolution of sulfoximines, providing chiral benzothiadiazine-1-oxides and recovered chiral sulfoximines with moderate to good enantioselectivities ( factors up to 36.6).

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http://dx.doi.org/10.1021/acs.joc.4c00623DOI Listing

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