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. 2003 Dec 11;5(25):4823-6.
doi: 10.1021/ol035776u.

Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates

Paul M Wehn  1 , Jihee Lee, J Du Bois
Affiliations

Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates

Paul M Wehn et al. Org Lett. .

Abstract

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]

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