A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

Eniko Forró, Tihamér Paál, Gábor Tasnádi, Ferenc Fülöp

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

Original languageEnglish
Pages (from-to)917-923
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number7-8
DOIs
Publication statusPublished - May 1 2006

Keywords

  • 4-aryl-substituted β-lactams
  • Enantioselectivity
  • Enzyme catalysis
  • Lipase
  • Ring cleavage
  • β-aryl-substituted β-amino acids

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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