1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes

Journal Article (Journal Article)

A new 1,3-dipolar cycloaddition of oxa(aza)bicyclic alkenes with nitrones has been developed. The operationally simple cycloaddition allows efficient synthesis of fused bicyclic tetrahydroisoxazoles bearing exo- and anti-five member heterocyclic rings (76-99% yields) without any catalyst and additive under mild conditions. The proposed concerted mechanism and the observed selectivity are investigated by DFT calculations of the reaction pathways. This mild and practical [3 + 2] cycloaddition provides an efficient route to access highly functionalized compounds.

Full Text

Duke Authors

Cited Authors

  • Yao, Y; Yang, W; Lin, Q; Li, H; Wang, L; Gu, F; Yang, D

Published Date

  • October 7, 2019

Published In

Volume / Issue

  • 6 / 19

Start / End Page

  • 3360 - 3364

Electronic International Standard Serial Number (EISSN)

  • 2052-4129

International Standard Serial Number (ISSN)

  • 2052-4110

Digital Object Identifier (DOI)

  • 10.1039/c9qo00660e

Citation Source

  • Scopus