Journal of Organic Chemistry p. 1895 - 1899 (1985)
Update date:2022-08-05
Topics:
Eguchi, Shoji
Furukawa, Yoshio
Suzuki, Takanori
Kondo, Kazumoto
Sasaki, Tadashi
et al.
The intramolecular cycloaddition of C-phenyl-N-(endo-bicyclo<3.2.1>oct-6-en-3-ylmethyl)nitrone (3) geneerated in situ from the corresponding hydroxylamine and benzaldehyde gave the adduct 4 in a high yield.Reductive cleavage of 4 afforded 2-endo-hydroxy-4-endo-phenyl-5-azatricyclo<5.3.1.03,9>undecane (6).The intramolecular cycloadditions of unsymmetrical N-(endo-bicyclo<2.2.1>hept-5-en-2-ylmethyl)nitrones (11a,b) and N-(endo-bicyclo<2.2.2>oct-5-en-2-ylmethyl)nitrones (23a,b) occurred regiospecifically to afford the adducts 12a, b and 24a,b, respectively.Reductive cleavage of these adducts provided a convenient route to functionalized 5-azatricyclo<5.2.1.03,8>decanes (15a,b, 16, 17) and 5-azatricyclo<5.3.1.03,8>undecanes (27a,b, 28, 29), respectively.The regiochemical and stereochemical assignments of 12a and 24a were proven by X-ray analysis of the methiodides 14a and 26a.
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Doi:10.1039/c39840001634
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(2019)Doi:10.1055/s-1984-30834
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