Atom-Economical and Stereoselective Difunctionalization of Electron-Withdrawing Alkynes with N-Trifluoromethylthiophthalimide

Difunctionalization: An N-methylmorpholine-catalyzed difunctionalization reaction of electron-withdrawing alkynes leading to α-SCF3-β-phthalimide unsaturated esters is described. N-Trifluoromethylthiophthalimide serves as both the nitrogen and SCF3 source. This difunctionalization reaction features high atom economy and excellent E/Z stereoselectivity.
An N-methylmorpholine-catalyzed aminotrifluoromethylthiolation of electron-withdrawing alkynes leads to α,β-unsaturated esters bearing a nitrogen and SCF3 groups. Here, N-trifluoromethylthiophthalimide serves as both the nitrogen and the SCF3 source. This difunctionalization reaction features mild reaction conditions, high atom economy, good yield (up to 93%) and excellent stereoselectivity (Z/E up to 28 : 1). This study provides a versatile approach for the synthesis of −SCF3-containing molecules (i. e. α-SCF3-β-amino acids).