Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting (CpRhIII)-Rh-X-Catalyzed C-H Functionalization

Chiral 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.


Publié dans:
Angewandte Chemie-International Edition, 58, 26, 8902-8906
Année
Jun 24 2019
Publisher:
Weinheim, WILEY-V C H VERLAG GMBH
ISSN:
1433-7851
1521-3773
Mots-clefs:
Laboratoires:




 Notice créée le 2019-07-24, modifiée le 2019-07-28


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