Open Access Open Access  Restricted Access Subscription Access

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 Bai
Cover Image

Abstract


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

Full Text: PDF Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv