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Enantioselective Synthesis of Chiral‐at‐Sulfur 1,2‐Benzothiazines by Cp x Rh III ‐Catalyzed C−H Functionalization of Sulfoximines
Author(s) -
Sun Yang,
Cramer Nicolai
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810887
Subject(s) - enantioselective synthesis , stereocenter , sulfur , cyclopentadienyl complex , catalysis , chemistry , rhodium , combinatorial chemistry , surface modification , stereochemistry , medicinal chemistry , organic chemistry
Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur‐chiral 1,2‐benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodium(III) complexes equipped with chiral cyclopentadienyl ligands and paired with suitable carboxylic acid additives engage in an enantiodetermining C−H activation directed by the sulfoximine group. Subsequent trapping of the rhodacycle with a broad range of diazoketones gives access to S‐chiral 1,2‐benzothiazines with synthetically highly attractive substitution patterns in good yields and enantioselectivities.