Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenesvia selective carbon–carbon bond cleavage

Abstract

A novel, mild, robust catalyst Y(OTf)₃ for C–C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefinvia a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.