1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes
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 addit...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2019-10, Vol.6 (19), p.3360-3364 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Yao, Yongqi Yang, Wen Lin, Qifu Yang, Weitao Li, Huanyong Wang, Lin Gu, Fenglong Yang, Dingqiao |
| description | 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. |
| doi_str_mv | 10.1039/C9QO00660E |
| format | Article |
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exo
- and
anti
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| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2019-10, Vol.6 (19), p.3360-3364 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Alkenes Catalysts Crystallography Cycloaddition Organic chemistry Selectivity |
| title | 1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes |
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