Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?

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Abstract

Twelve-membered cyclic cis- and trans-β-lactams 1b and 2b and the corresponding cyclic cis- and trans-β-amino acid enantiomers, 1a, 1c and 2a, 2c were prepared through the CAL-B-catalysed enantioselective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (±)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (±)-2. High enantioselectivities (E >200) were observed for the ring opening of both the cis- and trans-β-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 °C. The resolved β-lactams 1b and 2b (yield ≥47%) and β-amino acids 1a and 2a (yield ≥32%) could be easily separated.

Original languageEnglish
Pages (from-to)3193-3196
Number of pages4
JournalTetrahedron Asymmetry
Volume17
Issue number23
DOIs
Publication statusPublished - Dec 11 2006

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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