Experimental study demonstrates chiral phosphoric acid-catalyzed kinetic resolution of sulfoximines, highlighting accessible enantioenriched benzothiadiazine-1-oxides.
A catalytic kinetic resolution of sulfoximines has been developed through chiral phosphoric acid-catalyzed intramolecular dehydrative cyclizations. A variety of racemic sulfoximines bearing an ortho-amidophenyl moiety underwent asymmetric dehydrative cyclizations using this method, yielding both the recovered sulfoximines and benzothiadiazine-1-oxide products with good to high enantioselectivities (with s-factor up to 61). The diverse derivatizations of the chiral products into a wide range of S-stereogenic center-containing S,N-heterocycles have demonstrated the value of this method.
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Tang et al. (2024) studied this question.
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