A novel, mild, and highly stereoselective transformation of epoxides to azidohydrins by treatment with Et3Al/HN3 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.
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Mereyala et al. (1986) studied this question.
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