Jump to main content
Jump to site search

Issue 20, 2018
Previous Article Next Article

Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

Author affiliations

Abstract

Alkenylazaarenes as a novel class of dipolarophiles for 1,3-dipolar cycloaddition (1,3-DC) with nitrones was reported. A regioselectivity-switchable synthesis of multisubstituted isoxazolidines had been developed. In the presence of TMSOTf as catalyst, 4-substituted isoxazolidines were obtained as major products with high regio- and diastereoselectivities. Nonetheless, under microwave irradiation in a sealed system with water as solvent, exclusive 5-substituted isoxazolidines were produced in good yields.

Graphical abstract: Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Aug 2018, accepted on 02 Sep 2018 and first published on 03 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00826D
Org. Chem. Front., 2018,5, 2945-2949

  •   Request permissions

    Alkenylazaarenes as dipolarophiles in 1,3-dipolar cycloaddition of nitrones: regioselectivity-switchable and highly diastereoselective synthesis of multisubstituted isoxazolidines

    M. Tong, Y. Zhang, C. Qin, Y. Fu, Y. Liu, H. Li and W. Wang, Org. Chem. Front., 2018, 5, 2945
    DOI: 10.1039/C8QO00826D

Search articles by author

Spotlight

Advertisements