The synthesis of beta-N-tosylamino hydroxylamines via the ring opening of N-tosylaziridines and their use in reverse Cope cyclisations

Authors
O'Neil, IA Woolley, JC Southern, JM Hobbs, H
Citation
Ia. O'Neil et al., The synthesis of beta-N-tosylamino hydroxylamines via the ring opening of N-tosylaziridines and their use in reverse Cope cyclisations, TETRAHEDR L, 42(46), 2001, pp. 8243-8245
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
46
Year of publication
2001
Pages
8243 - 8245
Database
ISI
SICI code
0040-4039(20011112)42:46<8243:TSOBHV>2.0.ZU;2-Q
Abstract
N-Tosylated aziridines have been found to undergo high yielding and regiose lective ring opening with hydroxylamines in diethyl ether in the presence o f boron trifluoride diethyl ether complex to give beta -N-tosylamino hydrox ylamines. Suitable substrates were shown to undergo reverse-Cope cyclisatio ns to give amino functionalised pyrrolidine and piperidine N-oxides. (C) 20 01 Published by Elsevier Science Ltd.