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Electronic Effects on the cis/trans Selectivity in Formation of Isoxazolidine-Fused Eight-Membered Ring via an Intramolecular Nitrone-Alkene Cycloaddition

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Chemistry of Heterocyclic Compounds Aims and scope

An intramolecular nitrone-alkene cycloaddition involving in situ generated nitrones demonstrated reaction profiles different from those previously reported for pyrimidine system. Tuning the electron density of the benzene ring had a significant effect on cis/trans selectivity. These reactions were useful for the synthesis of novel tricyclic hexahydrobenzo[b]isoxazolo[3,4-f][1, 4]diazocin-4(1H)-ones and hexahydroisoxazolo[3,4-f]pyrido[3,2-b][1, 4]diazocin-4(1H)-one under mild reaction conditions in good yields

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Correspondence to Xu Bai.

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The Supplementary information file containing NMR spectra of the synthesized compounds is available at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 601–608

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Xiang, J., Zhu, T., Dang, Q. et al. Electronic Effects on the cis/trans Selectivity in Formation of Isoxazolidine-Fused Eight-Membered Ring via an Intramolecular Nitrone-Alkene Cycloaddition. Chem Heterocycl Comp 52, 601–608 (2016). https://doi.org/10.1007/s10593-016-1938-z

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  • DOI: https://doi.org/10.1007/s10593-016-1938-z

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