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The Control of Stereoselectivities in the Diels-Alder Reactions of N-Substituted Pyrroles and N-Substituted Isoindoles

Guangxing Sun, Douglas N. Butler, Ronald N. Warrener, Davor Margetic, John R. Malpass

Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland 4702, Australia

Abstract: Pyrrole and its N-substituted derivatives are not recognised as good Diels-Alder dienes and only a small number of cycloadditions involving pyrroles with dienophiles have been reported1-3. In this paper, we report new Diels-Alder reactions of N-acetyl and N-trimethylsilyl pyrroles and N-benzyl-tetra- fluoroisoindole with 7-oxanorbornadienomaleimide ONM 2(R=H) where the addition stereoselectivity is affected by the N-substituents of the pyrrole. Semiempirical (PM3) calculations in support of these findings are also presented along with preliminary results for the additions of the above pyrroles to the related dienophile ONM 2(R=Me).

Keywords: Pyrroles; Isoindoles; Diels-Alder Reactions; Stereoselectivities

1. Wirth D.; Lemal D.M. J. Am. Chem. Soc. 1982, 104, 847-848
2. Pitt, I. G.; Russell, R. A.; Warrener R. N. Synth. Commun. 1986, 16, 1627-1634
3. Chen, Z.; Trudell M. L. Chem. Rev. 1996, 96, 1179-1193
4. Warrener, R. N. Chemistry in Australia 1992, 59, 578-581

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