The “Non-Oxidative” Chloro-Pummerer Reaction: Novel Stereospecific Entry to Vicinal Chloroamines and Aziridines

Abstract

This article describes a new, useful synthetic tool, the “Non-Oxidative” Chloro-Pummerer Reaction (NOCPR), which allows for the use of enantiomerically pure α-Li alkylsulfoxides as chiral α-chloroalkyl carbanions with N-protected imines. In this reaction the sulfinyl group of N-alkoxycarbonyl-β-sulfinylamines derived from aryl-, fluoroalkyl- and alkylimines is displaced by a chlorine atom in a one-pot reaction with clean stereoinversion at carbon. Several 1,2-chloroamines produced via NOCPR were transformed into the corresponding aziridines. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)