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Synlett 1995; 1995(9): 891-892
DOI: 10.1055/s-1995-5125
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Synthesis of a New Constrained Homoserine

A. Avenoza, C. Cativiela* , M. A. Fernández-Recio, J. M. Peregrina
  • *Department of Organic Chemistry, Instituto de Ciencia de Materiales de Aragón. Universidad de Zaragoza-C.S.I.C. 50009 Zaragoza, Spain
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Publication Date:
31 December 2000 (online)

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A straightforward synthesis of a cyclic γ-hydroxy-α-amino acid analogue of homoserine was developed by directed hydroxylation via a dihydro-1,3-oxazine intermediate, starting from an unsaturated amino acid derivative, which can be easily obtained by a Diels-Alder reaction between methyl 2-acetamidoacrylate and 1,3-butadiene.

Methyl 2-acetamidoacrylate - 1,3-Butadiene - Diels-Alder - Hydroxylation - Homoserine