title: Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier.
abstract: The development of practical methods to access chiral nonracemic α-substituted ketones is of particular importance due to their ubiquitous nature. Unprecedented levels of enantioselectivity are reported for the synthesis of α-tosyloxy ketones, using enol esters and chiral iodine(III) reagents. The reaction can be performed under both stoichiometric and catalytic conditions. These results suggest widely different reaction mechanisms for the reaction of ketones versus enol esters, supporting recent computational insights.
authors.affiliation: University of Sherbrooke , Department of Chemistry, Centre in Green Chemistry and Catalysis, 2500 Boul de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
authors.forename: Benoit
authors.initials: B
authors.lastname: Basdevant
authors.affiliation: University of Sherbrooke , Department of Chemistry, Centre in Green Chemistry and Catalysis, 2500 Boul de l'Université, Sherbrooke, Québec J1K 2R1, Canada.
authors.forename: Claude Y
authors.initials: CY
authors.lastname: Legault