Lewis Acid-catalyzed [3+2]Cycloaddition of Alkynes with N-Tosylaziridines via Carbon-Carbon Bond Cleavage: Synthesis of Highly Substituted 3-Pyrrolines

A novel, efficient, and highly regloselective 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.