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Paper | Regular issue | Vol 55, No. 3, 2001, pp.469-485
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9094
Synthesis and Cycloaddition Reactions of New Captodative Olefins, N-Substituted 5-Alkylidene-1,3-oxazolidine-2,4-diones

Adriana Benavides, Rafael Martínez, Hugo A. Jiménez-Vázquez, Francisco Delgado, and Joaquin Tamariz*

*Departamento de Químíca Orgánica, Escuela Nacional de Ciencias Biológicas, I. P. N., Prol. Carpio y Plan de Ayala S/N,11340, Mexico, D.F.


An efficient and straightforward synthesis of the new captodative olefins N-substituted 5-alkylidene-1,3-oxazolidine-2,4-diones (8-10) is described, by a chemoselective oxidative cleavage of the novel exo-2-oxazolidinone dienes (3, 4, and 7), respectively. A study of the reactivity and selectivity of olefins (8-10), was carried out in Diels-Alder cycloadditions to cyclic and unsymmetric acyclic olefins. In all reactions, the corresponding adducts were obtained in high stereo- and regioselectivity. These results have been rationalized in terms of FMO theory by ab initio calculations. 1,3-Dipolar additions of nitrones to olefin (8a) were also highly regioselective, yielding only the C-5 substituted adducts.