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Synlett 1995; 1995(10): 1037-1039
DOI: 10.1055/s-1995-5167
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Lewis Acid Induced Rearrangement of 2,3-Epoxy Amines and Regiospecific Nucleophilic Trapping of Aziridinium Ion Intermediates with Amino Acid Esters: Synthesis of N(2-amino-3-hydroxyalkyl)-substituted Amino Acid Esters

Quanying Liu, Allan P. Marchington, Neville Boden, Christopher M. Rayner*
  • *School of Chemistry and Centre for Self-Organising Molecular Systems, University of Leeds, Leeds LS2 9JT, U.K.
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Publication Date:
31 December 2000 (online)

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Rearrangement of homochiral 2,3-epoxy amines by treatment with TMSOTf gives 3-trimethylsilyloxy-1,2-aziridinium triflates, which undergo efficient regiospecific ring opening at C-1 with amino acid ester nucleophiles to give N-(2-amino-3-hydroxyalkyl)-substituted amino acid esters.

aziridinium salt - epoxide - amino acid ester - amino alcohol - aminopeptidase inhibitor