Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates.
Oxidative C-H amination of chiral sulfamate esters using achiral Rh-carboxylate catalysts, PhI(OAc)(2), and MgO occurs in high yield and with good to excellent diastereocontrol. A number of examples are included to support a proposed transition state model that accounts for the observed stereoinduction. In addition, stereoselective intramolecular aziridination with substituted homoallyl sulfamates is demonstrated and is rationalized through an analogous stereochemical construct. [reaction: see text]
Wehn
Paul M
PM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA.
Lee
Jihee
J
Du Bois
J
J
D000586:Amination; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000737:chemistry*
D004952:Esters; D013451:Sulfonic Acids; C005741:sulfamic acid; D012238:Rhodium