The 'non-oxidative' chloro-Pummerer reaction: a highly stereoselective entry to beta-chloro amines and aziridines

Authors
Volonterio, A Bravo, P Pesenti, C Zanda, M
Citation
A. Volonterio et al., The 'non-oxidative' chloro-Pummerer reaction: a highly stereoselective entry to beta-chloro amines and aziridines, TETRAHEDR L, 42(24), 2001, pp. 3985-3988
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
24
Year of publication
2001
Pages
3985 - 3988
Database
ISI
SICI code
0040-4039(20010611)42:24<3985:T'CRAH>2.0.ZU;2-3
Abstract
Enantiomerically pure a-Li alkyl-sulfoxides can be used as chiral cl-chloro alkyl carbanions with N-protected imines by means of the 'non-oxidative' ch loro-Pummerer reaction (NOCPR). This novel methodology allows for a one-pot displacement of a sulfinyl group by chlorine from N-alkoxycarbonyl beta -s ulfinylamines derived from aryl, fluoroalkyl and alkyl imines, with clean s tereoinversion at carbon. Several 1,2-chloroamines produced via NOCPR were transformed into the corresponding aziridines. (C) 2001 Elsevier Science Lt d. All rights reserved.