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Synlett 1992; 1992(1): 45-47
DOI: 10.1055/s-1992-21260
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Regio- and Stereocontrolled Nucleophilic Ring Opening of Chiral Oxazolidines by Diethylaluminum Cyanide. A Short and Efficient Route to Enantiomerically Enriched α-Amino Esters

Celia Andrés* , Alicia Maestro, Rafael Pedrosa, Alfonso Pérez-Encabo, Martina Vicente
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n., E-47011 Valladolid, Spain
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Publication Date:
18 September 2002 (online)

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α-Amino esters 7 are prepared in good chemical yield and enantiomeric excess (53-86%) by ethanolysis and subsequent debenzylation of the α-amino nitriles 5 obtained by regio- and stereocontrolled ring opening of N-benzyl-2-phenylglycinol-derived oxazolidines 4 (2-alkyl-3-benzyl-4-phenyloxazolidines) with diethylaluminum cyanide.

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