Preparation of Vicinal Azidohydrins by Reaction of Oxiranes with Triethylaluminium/Hydrogen Azide

Abstract

Abstract A novel, mild, and highly stereoselective transformation of epoxides to azidohydrins by treatment with Et 3 Al/HN 3 in toluene is described. As an example for the versatility of the reaction, a polyfunctional compound, 14,15‐epoxy‐14,15‐dihydromilbemycin D ( 1 ), was transformed to 14‐azido‐14,15‐dihydro‐15‐hydroxymilbemycin D ( 2 ) in 61% yield.