title: Study of the Reactivity of [Hydroxy(tosyloxy)iodo]benzene Toward Enol Esters to Access α-Tosyloxy Ketones.
abstract: The reactivity of enol esters toward [hydroxy(tosyloxy)iodo]benzene (HTIB) was assessed. These substrates were found to be rapidly converted in high yields to their corresponding α-tosyloxy ketones. This transformation demonstrates that these substrates can act as ketone surrogates. The scope of the method was investigated and aromatic, aliphatic, and cyclic enol esters were found to be suitable substrates for the reaction. The relative reactivity of a model substrate toward HTIB and m-CPBA was investigated, and it was found that the reaction could be performed under catalytic conditions.
authors.affiliation: Université of Sherbrooke, CCVC, Department of Chemistry, 2500 Boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
authors.forename: Benoit
authors.initials: B
authors.lastname: Basdevant
authors.affiliation: Université of Sherbrooke, CCVC, Department of Chemistry, 2500 Boul. de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
authors.forename: Claude Y
authors.initials: CY
authors.lastname: Legault