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

Chemical Communications Pub Date: 2011-03-24 DOI: 10.1039/C1CC10926J

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.

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