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Preparation of Vicinal Azidohydrins by Reaction of Oxiranes with Triethylaluminium/Hydrogen Azide
Author(s) -
Babu Mereyala Hari,
Frei Bruno
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690222
Subject(s) - chemistry , vicinal , yield (engineering) , azide , stereoselectivity , epoxy , toluene , epoxide , organic chemistry , medicinal chemistry , catalysis , materials science , metallurgy
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.
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