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Synlett 1995; 1995(10): 1037-1039
DOI: 10.1055/s-1995-5167
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
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Publication History
Publication Date:
31 December 2000 (online)
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