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Chemistry of Heterocyclic Compounds

, Volume 52, Issue 8, pp 601–608 | Cite as

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

  • Jinbao Xiang
  • Tong Zhu
  • Qun Dang
  • Xu BaiEmail author
Article

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

Keywords

isoxazolidines tricyclic compounds cis/trans selectivity eight-membered rings electronic effects fused-ring systems nitrone-alkene cycloaddition 

Notes

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences and The College of ChemistryJilin UniversityChangchunP. R. China

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