Lewis acid-catalyzed [3 + 2]cyclo-addition of alkynes with N-tosyl-aziridines via carbon-carbon bond cleavage: synthesis of highly substituted 3-pyrrolines

Abstract

A novel, efficient, and highly regioselective Lewis acid-catalyzed [3 + 2] cycloaddition of alkynes with azomethine ylides, which are easily obtained from N-tosylaziridines via C-C bond heterolysis at room temperature was developed. Moderate enantioselectivity (70% ee) can be achieved by the application of the commercially available chiral Pybox 7 as the ligand.