Annelation of cyclic dienes to amino-and azabicyclic diols by iterated cycloadditions of nitrones

JT Bailey, I Berger, R Friary…

Index: Bailey, J. T.; Berger, I.; Friary, R.; Puar, M. S. Journal of Organic Chemistry, 1982 , vol. 47, # 5 p. 857 - 863

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Citation Number: 9

Abstract

Results Bimolecular cycloadditions of simple nitrones to cyclic 1, 5-, 1, 4-, and 1, 3-dienes, N- oxidations, and intramolecular cycloadditions formed tricyclic isoxazolidines 16-18, 25, and 29. Hydrogenolyses of the tricycloadducts yielded the desired amino-and azabicyclic diols. N-Methylnitrone changed 1, 5-cyclooctadiene to three kinds of products, 1, 2-3, and 4. N- Phenylnitrone and l, 5-cyclooctadiene gave diol 5 after catalytic reduction. Reactions of N- ...