X=Y-ZH systems as potential 1,3-dipoles. Part 53: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles

Authors
Dondas, HA Cummins, JE Grigg, R Thornton-Pett, M
Citation
Ha. Dondas et al., X=Y-ZH systems as potential 1,3-dipoles. Part 53: Sequential nucleophilic ring opening-1,3-dipolar cycloaddition reactions of Z-oxime anions with aziridines and dipolarophiles, TETRAHEDRON, 57(37), 2001, pp. 7951-7964
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
37
Year of publication
2001
Pages
7951 - 7964
Database
ISI
SICI code
0040-4020(20010910)57:37<7951:XSAP1P>2.0.ZU;2-8
Abstract
Nucleophilic ring opening of aziridines involving attack of the nitrogen at om of Z-oxime anions generates nitrones which are then trapped in 1,3-dipol ar cycloaddition reactions with N-methylmaleimide to afford 1: 1 mixture of endo- and exo-cycloadducts. (C) 2001 Elsevier Science Ltd. All rights rese rved.