359761-56-1Relevant academic research and scientific papers
The 'non-oxidative' chloro-Pummerer reaction: A highly stereoselective entry to β-chloro amines and aziridines
Volonterio, Alessandro,Bravo, Pierfrancesco,Pesenti, Cristina,Zanda, Matteo
, p. 3985 - 3988 (2001)
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.
The "Non-Oxidative" Chloro-Pummerer Reaction: Novel stereospecific entry to vicinal chloroamines and aziridines
Volonterio, Alessandro,Bravo, Pierfrancesco,Panzeri, Walter,Pesenti, Cristina,Zanda, Matteo
, p. 3336 - 3340 (2007/10/03)
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.
