Advanced procedure for the enzymatic ring opening of unsaturated alicyclic β-lactams

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Abstract

Enantiopure β-amino acids 1a-4a and β-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic β-lactams (±)-1-(±)-4. High enantioselectivities (E>200) were observed when the reactions were performed with 1equiv of water in iPr2O at 70°C. The resolved (1R,2S)-amino acids (yield≥45%) and (1S,5R)-, (1S,6R)- and (1S,8R)-lactams (yield≥47%) could be easily separated. The ring opening of lactam enantiomers 1b-4b with 18% HCl afforded the corresponding β-amino acid hydrochlorides 1c·HCl-4c·HCl (ee>95%).

Original languageEnglish
Pages (from-to)2875-2880
Number of pages6
JournalTetrahedron Asymmetry
Volume15
Issue number18
DOIs
Publication statusPublished - Sep 20 2004

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ASJC Scopus subject areas

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

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