Summary.
The (Z)-N-substituted 4-methylene-5-propylidene-2-oxazolidinone dienes were prepared by a one-step synthesis, starting from 2,3-hexanedione and isocyanates. Diels-Alder cycloadditions of these dienes were carried out in the presence of the dienophiles methyl vinyl ketone, methyl propiolate, and a captodative olefin, under conditions such as solvents of high polarity, Lewis acid catalysis, and non-conventional energy sources. The reactions carried out either with mixtures of H2O/MeOH or under BF3·Et2O catalysis yielded the highest regio- and stereoselectivities. The use of ionic liquids, microwaves, and ultrasound did not significantly increase the selectivity.
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Fuentes, A., Martínez-Palou, R., Jiménez-Vázquez, H. et al. Diels-Alder Reactions of 2-Oxazolidinone Dienes in Polar Solvents Using Catalysis or Non-conventional Energy Sources. Monatshefte für Chemie 136, 177–192 (2005). https://doi.org/10.1007/s00706-004-0244-0
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DOI: https://doi.org/10.1007/s00706-004-0244-0