Enantioselective α-Trifluoromethylthiolation of Carbonyl Compounds with AgSCF3and Trichloroisocyanuric Acid

Autor: Wang, Yakun, Wang, Yingying, Guo, Wenwen, Zhang, Yizhe, Du, Xiaoyu, Song, Yan, Wang, Wenhui, Liu, Zhiang, Duan, Yingchao, Zhang, Tao
Zdroj: The Journal of Organic Chemistry; June 2024, Vol. 89 Issue: 11 p8011-8022, 12p
Abstrakt: We successfully developed an enantioselective trifluoromethylthiolation of structurally diverse carbonyl compounds. Trichloroisocyanuric acid and AgSCF3were employed to generate active electrophilic trifluoromethylthio species in situ for asymmetric C-SCF3bond formation. A broad variety of chiral SCF3-carbon nucleophiles (pyrazolones, β-keto esters, and β-keto amides) were obtained in excellent yields with high enantioselectivities (up to 92% ee) by Cinchona alkaloid derived squaramide catalysts. The reaction exhibits high efficiency, good enantioselectivity, and high functional group tolerance, which provided a novel and efficient way for asymmetric synthesis of trifluoromethylthiolated carbonyl compounds.
Databáze: Supplemental Index