Stereocontrolled synthesis of five diastereomers of trimethyl 3-aminocyclopentane-1,2,4-tricarboxylates

Ferenc Miklós, István M. Mándity, Reijo Sillanpää, Ferenc Fülöp

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The sterically controlled oxidative cleavage of N-protected diexo- and diendo-substituted norbornene β-amino acids/esters resulted in four trimethyl 3-aminocyclopentane-1,2,4-carboxylate diastereomers. The sodium methoxide mediated isomerization of the four diastereomers in all cases yielded the thermodynamically most stable all-trans stereoisomer as a single product.

Original languageEnglish
Pages (from-to)3769-3772
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number29
DOIs
Publication statusPublished - Jul 17 2013

Keywords

  • Epimerization
  • Isomerization
  • Oxidative cleavage
  • Potassium permanganate oxidation
  • β-Aminotricarboxylic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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