Solid-Phase Organic Synthesis of Methyl Isoxazole-5-carboxylates Based on Wang Resin–Bound 1-Phenylselenoacrylate

Abstract

A novel Wang resin–bound 1-phenylselenoacrylate reagent has been developed and used as dipolarophile for the 1,3-dipolar cycloaddition with nitrile oxides to the regioselective synthesis of methyl 3-substituted isoxazole-5-carboxylates in good yields and purities.

GRAPHICAL ABSTRACT

Keywords:

• 1,3-Dipolar cycloaddition
• methyl 3-substituted-isoxazole-5-carboxylate
• oxidation–elimination
• solid–phase organic synthesis
• Wang resin–bound 1-phenylselenoacrylate

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 21062007), NSF of Jiangxi Province (No. 2009GZH0016) and the Research Program of Jiangxi Province Department of Education (Nos. GJJ10385 and GJJ11380).

Notes

^a Overall yields based on Wang resin–bound 1-phenylselenoacrylate 4 (0.80 mmol Se/g).

^b Determined by HPLC of crude cleavage product.