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Reductive Ring Opening of Ephedrine and Pseudo-Ephedrine-Derived Oxazolidinium Methiodides by Sodium Borohydride. A Direct Access to New Chiral Amine-Borane Adducts
Authors:Celia Andres  Manuel Delgado  Rafael Pedrosa
Institution:Departamento de Química Orgánica, Facultad de Ciencias , Universidad de Valladolid , Dr. Mergelina s/n, 47011, Valladolid, Spain
Abstract:Sodiun borohydride reacts with oxazolidinium methiodides derived from ephedrine and pseudoephedrine, in ethereal solvents, cleaving regioselectively the C-N bond of the ring and leading, in good yields, to chiral amine-borane adducts of know absolute configuration. The 1HNMR data allow to predict the most stable conformation.
Keywords:Biginelli reaction  dihydropyrimidinones  magnesium chloride hexahydrate  one‐pot condensation  solvent‐free
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