Enantioselective Iodine(III)-Mediated Synthesis of α-Tosyloxy Ketones: Breaking the Selectivity Barrier

Article abstract of DOI:10.1021/acs.orglett.5b02501

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.