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

Publication ,  Journal Article
Yao, Y; Yang, W; Lin, Q; Li, H; Wang, L; Gu, F; Yang, D
Published in: Organic Chemistry Frontiers
October 7, 2019

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.

Duke Scholars

Published In

Organic Chemistry Frontiers

DOI

EISSN

2052-4129

ISSN

2052-4110

Publication Date

October 7, 2019

Volume

6

Issue

19

Start / End Page

3360 / 3364

Related Subject Headings

  • 3405 Organic chemistry
  • 0305 Organic Chemistry
 

Citation

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ICMJE
MLA
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Yao, Y., Yang, W., Lin, Q., Li, H., Wang, L., Gu, F., & Yang, D. (2019). 1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes. Organic Chemistry Frontiers, 6(19), 3360–3364. https://doi.org/10.1039/c9qo00660e
Yao, Y., W. Yang, Q. Lin, H. Li, L. Wang, F. Gu, and D. Yang. “1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes.” Organic Chemistry Frontiers 6, no. 19 (October 7, 2019): 3360–64. https://doi.org/10.1039/c9qo00660e.
Yao Y, Yang W, Lin Q, Li H, Wang L, Gu F, et al. 1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes. Organic Chemistry Frontiers. 2019 Oct 7;6(19):3360–4.
Yao, Y., et al. “1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes.” Organic Chemistry Frontiers, vol. 6, no. 19, Oct. 2019, pp. 3360–64. Scopus, doi:10.1039/c9qo00660e.
Yao Y, Yang W, Lin Q, Li H, Wang L, Gu F, Yang D. 1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes. Organic Chemistry Frontiers. 2019 Oct 7;6(19):3360–3364.
Journal cover image

Published In

Organic Chemistry Frontiers

DOI

EISSN

2052-4129

ISSN

2052-4110

Publication Date

October 7, 2019

Volume

6

Issue

19

Start / End Page

3360 / 3364

Related Subject Headings

  • 3405 Organic chemistry
  • 0305 Organic Chemistry