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Synthesis 1989; 1989(4): 256-261
DOI: 10.1055/s-1989-27216
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Amino Acids and Peptides; 70.1 Optically Active α-Amino Acids, N-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acid from 2,3-Epoxy Alcohols

Ulrich Schmidt* , Mathias Respondek, Albrecht Lieberknecht, Jürgen Werner, Peter Fischer
  • *Institut für Organische Chemie, Biochemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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Trichloroacetimidic esters of 2,3-epoxy alcohols are transformed into oxazolines 5 and dihydrooxazines 6, respectively, depending on the structure of the educts and the catalyst. The five-membered ring compounds 5 are transformed into erythro-α-amino-β-hydroxy acids (60-70% from epoxy alcohols) via oxazolidinones 11, 12, and 13. α-Amino acids and α-substituted α-amino acids 10 as well as the corresponding aldehydes 9 are obtained from the dihydrooxazines 6 (50-60% from epoxy alcohols).