Synthesis of (1S)-1-amino-2, 2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2, 2, 2-trifluoroethyl) 2, 2-dimethylcyclopropane-1, 1-dicarboxylate

Antonio Salgado, Tom Huybrechts, Annelies Eeckhaut, Johan Van der Eycken, Zsolt Szakonyi, Ferenc Fülöp, Alexey Tkachev, Norbert De Kimpe

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Hydrolysis of bis(2, 2, 2-trifluoroethyl) 2, 2-dimethylcyclopropane-1, 1-dicarboxylate with pig liver esterase afforded (1R)-2, 2-dimethyl-1-(2, 2, 2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2, 2, 2-trifluoroethyl-2, 2-dimethyl-1-[(N-ethoxycarbonyl)amino]- cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2, 2-dimethylcyclopropane-1-carboxylic acid.

Original languageEnglish
Pages (from-to)2781-2786
Number of pages6
JournalTetrahedron
Volume57
Issue number14
DOIs
Publication statusPublished - Apr 2 2001

Keywords

  • 1-Aminocyclopropane-1-carboxylic acid
  • 2, 2-DimethylACC
  • Curtius rearrangement
  • Enzymatic hydrolysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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