Cobalt(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective Synthesis of Benzothiadiazine-1-oxides via C-H Activation.

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.
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