Catalytic enantioselective α-tosyloxylation of ketones using iodoaryloxazoline catalysts: insights on the stereoinduction process.

ABSTRACT

A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated α-tosyloxylation of ketone derivatives. The α-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.