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Asymmetric Synthesis of Functionalized Prolines by Diastereoselective 1,3-Dipolar Cycloaddition Using Chiral Oxazinone Derivatives
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1  Departamento de Quimica Organica, Universidad de Alicante. E-03080 Alicante, Spain

Abstract: The reaction of (5S,6S)-6-isopropyl-5-phenyl-1,4-oxazin-2-ones from glycine and alanine with formaldehyde in the presence of electron-deficient olefins afforded the corresponding adducts obtained by a diastereoselective 1,3-dipolar cycloaddition of the chiral azomethine ylids. Hydrolysis of these adducts allows the synthesis of enantiomerically enriched functionalized prolines
Keywords: Amino acids, oxazinones, 1,3-dipolar cycloadditions, prolines