Nucleophilic ring opening of 3-benzyl-1,3-oxazinanes by Reformatsky reagents. A synthesis of β-amino ester derivatives

Article abstract of DOI:10.1055/s-1990-27092

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, 1 h) leading regioselectively to 3-substituted ethyl 3-[(3-hydroxypropyl)benzylamino]propanoates in high yield.