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Communication | Regular issue | Vol 48, No. 9, 1998, pp.1753-1757
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8263
Regioselective Ring-Opening of 2,3-Epoxy Alcohols with Tetramethylammonium Triacetoxyborohydride

Toshio Honda* and Hirotake Mizutani

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


Treatment of 2,3-epoxy alcohols with tetramethylammonium triacetoxyborohydride afforded the ring-opening products at the C-3 position, regioselectively, where the presence of Me4NBH(OAc)3 increased the reaction rate and regioselectivity by forming the chelation intermediate between the metal center and the epoxy alcohol oxygens.