Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused β-lactams in an organic solvent

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Abstract

(Matrix presented) A highly efficient and very simple method was developed for the synthesis of enantiopure β-amino acids (e.g. cispentacin) and β-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic β-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase (lipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in diisopropyl ether at 60°C. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.

Original languageEnglish
Pages (from-to)1209-1212
Number of pages4
JournalOrganic Letters
Volume5
Issue number8
DOIs
Publication statusPublished - Apr 17 2003

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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