Regioselectivity in the ring opening of epoxides for the synthesis of aminocyclitols from D-(-)-quinic acid.
نویسندگان
چکیده
Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.
منابع مشابه
Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water
Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.
متن کاملB-podands as efficient catalysts for the ring opening of epoxides in water: A versatile and atom economical method for the synthesis of vicinal azidoalcohols
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The regioselective ring opening of styrene oxide using elemental iodine and bromine in the presence of disulfides as new catalysts was studied. The conductivity titration and UV spectroscopy were used to study the interaction of iodine with these catalysts. The results indicate that disulfide 11 is efficient in polyiodide formation, and can catalyze this reaction in excellent yield and high reg...
متن کاملDisulfide catalyzed the highly regioselective conversion of epoxides to halohydrins with elemental halogens
The regioselective ring opening of styrene oxide using elemental iodine and bromine in the presence of disulfides as new catalysts was studied. The conductivity titration and UV spectroscopy were used to study the interaction of iodine with these catalysts. The results indicate that disulfide 11 is efficient in polyiodide formation, and can catalyze this reaction in excellent yield and high reg...
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ورودعنوان ژورنال:
- Molecules
دوره 17 4 شماره
صفحات -
تاریخ انتشار 2012