Cobalt(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective Synthesis of Benzothiadiazine‐1‐oxides via C−H Activation
Yuuki Hirata, Daichi Sekine, Yoshimi Kato, Luqing Lin, M. Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Abstract
Abstract Among sulfoximine derivatives containing a chiral sulfur center, benzothiadiazine‐1‐oxides are important for applications in medicinal chemistry. Here, we report that the combination of an achiral cobalt(III) catalyst and a pseudo‐ C 2 ‐symmetric H 8 ‐binaphthyl chiral carboxylic acid enables the asymmetric synthesis of benzothiadiazine‐1‐oxides from sulfoximines and dioxazolones via enantioselective C−H bond cleavage. With the optimized protocol, benzothiadiazine‐1‐oxides with several functional groups can be accessed with high enantioselectivity.
Topics & Concepts
BenzothiadiazineEnantioselective synthesisCobaltChemistryCatalysisCarboxylic acidCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms