Synthesis and cycloaddition reactions of new captodative olefins N-substituted 5-alkylidene-1,3-oxazolidine-2,4-diones

Citation
A. Benavides et al., Synthesis and cycloaddition reactions of new captodative olefins N-substituted 5-alkylidene-1,3-oxazolidine-2,4-diones, HETEROCYCLE, 55(3), 2001, pp. 469-485
Citations number
73
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
0385-5414 → ACNP
Volume
55
Issue
3
Year of publication
2001
Pages
469 - 485
Database
ISI
SICI code
0385-5414(20010301)55:3<469:SACRON>2.0.ZU;2-P
Abstract
An efficient and straightforward synthesis of the new captodative olefins N -substituted 5-alkylidene-1,3-oxazolidine-2,4-diones (8-10) is described, b y a chemoselective oxidative cleavage of the novel exo-2-oxazolidinone dien es (3, 4, and 7), respectively. A study of the reactivity and selectivity o f olefins (8-10), was carried out in Diels-Alder cycloadditions to cyclic a nd unsymmetric acyclic olefins. In all reactions, the corresponding adducts were obtained in high stereo- and regioselectivity. These results have bee n rationalized in terms of FMO theory by ab initio calculations. 1,3-Dipola r additions of nitrones to olefin (8a) were also highly regioselective, yie lding only the C-5 substituted adducts.