Five-component equilibria of ring-chain tautomeric mixtures derived from 2-amino-1-phenyl-1,3-propanediol diastereomers

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Abstract

In the reactions of (1R*,2S*)- or (1S,2S)-2-amino-1-phenyl-1,3- propanediol with aromatic aldehydes, five-component ring-chain tautomerie mixtures were formed, involving C-2 epimers of structurally isomeric oxazolidines and the corresponding Schiff base. These multicomponent tautomeric equilibria could be described by the equation log K(x) = ρσ+ + log K(X=H).

Original languageEnglish
Pages (from-to)12887-12896
Number of pages10
JournalTetrahedron
Volume54
Issue number42
DOIs
Publication statusPublished - Oct 15 1998

Keywords

  • Amino alcohols
  • Oxazolidines
  • Stereochemistry
  • Tautomerism

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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