The ‘non-oxidative’ chloro-Pummerer reaction: a highly stereoselective entry to β-chloro amines and aziridines

Enantiomerically pure α-Li alkyl-sulfoxides can be used as chiral α-chloroalkyl carbanions with N-protected imines by means of the ‘non-oxidative’ chloro-Pummerer reaction (NOCPR). This novel methodology allows for a one-pot displacement of a sulfinyl group by chlorine from N-alkoxycarbonyl β-sulfinylamines derived from aryl, fluoroalkyl and alkyl imines, with clean stereoinversion at carbon. Several 1,2-chloroamines produced via NOCPR were transformed into the corresponding aziridines.