Synthesis of Isoxazolidinyl Epoxides by Oxone Treatment of 2,3-Dihydroisoxazoles in Acetone–Water Solution: A New Stereoselective Approach to Hydroxy-Substituted Isoxazolidines

Abstract

A practical and efficient synthesis of new class of isoxazoli­dinyl epoxides by direct treatment of 4,5-unsubstituted 2,3-dihydroisoxazoles with Oxone and NaHCO₃ in acetone/water solution is described. All epoxidation reactions proceed with excellent anti-selectivity and provide stable products in very good yields. A concept for the development of stereoselective approach to 3,4-trans-hydroxy-substituted isoxazolidines, namely triazole derivatives as important molecules in medicinal chemistry is presented. The synthesis is characterized by highly syn-stereoselective conversion of epoxides to anomeric bromoisoxazolidines, which are found to be powerful reaction intermediates for the coupling reactions with various nucleophiles.

Key words

heterocycles - isoxazolidines - epoxides - triazoles - diastereoselectivity - aza-Michael addition - organocatalysis

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