Issue 19, 2019

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
17 May 2019
Accepted
13 Aug 2019
First published
15 Aug 2019

Org. Chem. Front., 2019,6, 3360-3364

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

Y. Yao, W. Yang, Q. Lin, W. Yang, H. Li, L. Wang, F. Gu and D. Yang, Org. Chem. Front., 2019, 6, 3360 DOI: 10.1039/C9QO00660E

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