Diastereoselective synthesis of cis-2,5-disubstituted pyrrolidine N-oxidesby the retro-Cope elimination

Authors
Bagley, MC Tovey, J
Citation
Mc. Bagley et J. Tovey, Diastereoselective synthesis of cis-2,5-disubstituted pyrrolidine N-oxidesby the retro-Cope elimination, TETRAHEDR L, 42(2), 2001, pp. 351-353
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
2
Year of publication
2001
Pages
351 - 353
Database
ISI
SICI code
0040-4039(20010108)42:2<351:DSOCPN>2.0.ZU;2-9
Abstract
Nitrones were reacted with 3-butenylmagnesium bromide to give alkenylhydrox ylamines that were cyclised by retro-Cope elimination. Heating the diastere omeric mixtures of pyrrolidine N-oxides in the absence of solvent affected a highly diastereoselective isomerisation to provide the cis-2,5-disubstitu ted products in excellent yield. (C) 2000 Elsevier Science Ltd. All rights reserved.