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Synthesis 1990; 1990(11): 1057-1058
DOI: 10.1055/s-1990-27092
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Nucleophilic Ring Opening of 3-Benzyl-1,3-oxazinanes by Reformatsky Reagents. A Synthesis of ß-Amino Ester Derivatives

Angel Alberola* , Maria A. Alvarez, Celia Andrés, Alfonso González, Rafael Pedrosa
  • *Departamento de Quimica Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n. E-47011-Valladolid, Spain
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Publication Date:
17 September 2002 (online)

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2-Substituted 3-benzyl-1,3-oxazinanes react with the Reformatsky reagent derived from ethyl 2-bromoacetate and zinc, using very mild conditions (0°C, 1h) leading regioselectively to 3-substituted ethyl 3-[(3-hydroxypropyl)benzylamino] propanoates in high yield.