Cycloaddition reactions of C,N-diphenylnitrone to methylene-gamma-butyrolactones

Authors
Cacciarini, M Cordero, FM Faggi, C Goti, A
Citation
M. Cacciarini et al., Cycloaddition reactions of C,N-diphenylnitrone to methylene-gamma-butyrolactones, MOLECULES, 5(4), 2000, pp. 637-647
Citations number
40
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
MOLECULES
ISSN journal
14203049 → ACNP
Volume
5
Issue
4
Year of publication
2000
Pages
637 - 647
Database
ISI
SICI code
1420-3049(200004)5:4<637:CROCTM>2.0.ZU;2-R
Abstract
Cycloaddition of C,N-diphenylnitrone to alpha-methylene-gamma-butyrolactone afforded two diastereomeric 5-spirosubstituted isoxazolidines with high se lectivity. Structural assignment was ascertained by NMR studies and an X-ra y diffraction experiment on a single crystal of the major isomer and the di astereoselectivity was rationalized on examination of the alternative trans ition states leading to the two diastereoisomers.