Enantioselective Electrophilic Trifluoromethylthiolation of β-Keto-esters: A Case of Reactivity and Selectivity Bias for Organocatalysis

摘要

The incorporation of an SCF, group into small molecules is of great interest to the pharmaceutical and agrochemical industries, because the high lipophilicity and high electron-withdrawing character of the SCF3 group may have beneficial effects on the pharmacokinetics of drug molecules. Thus, the development of efficient methods for the introduction of a SCF3 group into organic compounds has recently become a subject of intense study and tremendous progress has been achieved in the transition-metal-catalyzed trifluoromethylthiolation of aryl, alkenyl, or alkynyl substrates under mild conditions. In particular, there has been a growing interest in the stereoselective introduction of SCF3 groups to generate chiral centers. While there is a growing number of methods for the catalytic enantioselective trifluor-omethylation, to the best of our knowledge, the analogous catalytic asymmetric direct trifluoromethylthiolation has never been reported.