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The “Non‐Oxidative” Chloro‐Pummerer Reaction: Novel Stereospecific Entry to Vicinal Chloroamines and Aziridines
Author(s) -
Volonterio Alessandro,
Bravo Pierfrancesco,
Panzeri Walter,
Pesenti Cristina,
Zanda Matteo
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200210)2002:19<3336::aid-ejoc3336>3.0.co;2-t
Subject(s) - chemistry , carbanion , vicinal , stereospecificity , pummerer rearrangement , aryl , carbon atom , oxidative phosphorylation , organic chemistry , medicinal chemistry , stereochemistry , computational chemistry , ring (chemistry) , catalysis , acetic anhydride , biochemistry , alkyl
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)