Brauns, MarcusCramer, Nicolai2019-07-242019-07-242019-07-242019-06-2410.1002/anie.201904543https://infoscience.epfl.ch/handle/20.500.14299/159304WOS:000474806700049Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C-H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cp-x ligand selectively participates in conjunction with phthaloyl phenylalanine in the C-H activation of just one of the two sulfoximine enantiomers. The intermediate reacts with various diazo compounds, providing access to chiral 1,2-benzothiazines with synthetically valuable substitution patterns. Both sulfoximines and 1,2-benzothiazines were obtained in high yields and excellent enantioselectivity, with s-values of up to 200. The utility of the method is illustrated by the synthesis of the key intermediates of two pharmacologically relevant kinase inhibitors.Chemistry, MultidisciplinaryChemistryasymmetric catalysischiral cp ligandskinetic resolutionrhodiumsulfoximinesone-potactivationligandsacidsiodinationdiscoveryamidationsannulation4-alkynalsinhibitortext::journal::journal article::research article