Synthesis and reactivity of 1-pyrroline-5-carboxylate ester 1-oxides

Authors
Black, DS Edwards, GL Evans, RH Keller, PA Laaman, SM
Citation
Ds. Black et al., Synthesis and reactivity of 1-pyrroline-5-carboxylate ester 1-oxides, TETRAHEDRON, 56(13), 2000, pp. 1889-1897
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
13
Year of publication
2000
Pages
1889 - 1897
Database
ISI
SICI code
0040-4020(20000324)56:13<1889:SARO1E>2.0.ZU;2-0
Abstract
Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepar ed via reductive cyclisation of the corresponding gamma-nitro carbonyl comp ounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselecti vely alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a he tero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved .