Issue 20, 2018

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
06 Leq 2018
Accepted
02 Way 2018
First published
03 Way 2018

Org. Chem. Front., 2018,5, 2945-2949

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

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