Direct oxidation of Δ2-isoxazolines synthesis by metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition with “activated” DMSO

Abstract

A series of 4-hydroxyl-Δ2-isoxazol-6(6aH)-one derivatives was prepared by magnesium ion-mediated diastereoface-selective 1,3-dipolar cycloaddition of aromatic nitrile oxides with pyrrolidinone derivatives. The reaction of 4-hydroxyl-Δ2-isoxazol-6(6aH)-one derivatives with dimethylsulfoxide and oxalyl chloride under Swern conditions led to a Δ2-isoxazole-4,6(5H,6aH)-dione.

Keywords

• 1,3-Dipolar cycloaddition
• Δ2-Isoxazol-6(6aH)-one
• Δ2-Isoxazole-4,6(5H,6aH)-dione
• Stereoselectivity
• Swern oxidation