Diastereo selective cycloaddition of alkylidenecyclopropane nitrones from palladium(0)-catalyzed nucleophilic substitution of asymmetric 1-alkenylcyclopropyl esters by amino acids

Authors
Pisaneschi, F Cordero, FM Goti, A Paugam, R Ollivier, J Brandi, A Salaun, J
Citation
F. Pisaneschi et al., Diastereo selective cycloaddition of alkylidenecyclopropane nitrones from palladium(0)-catalyzed nucleophilic substitution of asymmetric 1-alkenylcyclopropyl esters by amino acids, TETRAHEDR-A, 11(4), 2000, pp. 897-909
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
4
Year of publication
2000
Pages
897 - 909
Database
ISI
SICI code
0957-4166(20000310)11:4<897:DSCOAN>2.0.ZU;2-N
Abstract
The asymmetric construction of perhydropyrrolo[3,4-b]pyridine derivatives w as performed by chemo- and regioselective formation of enantiopure alkylide necyclopropane nitrones, followed by diastereoselective intramolecular 1,3- dipolar cycloaddition. The resulting spirocyclopropane isoxazolidines then underwent thermally induced regioselective ring expansion into optically ac tive diazaheterocycles. (C) 2000 Elsevier Science Ltd. All rights reserved.