An efficient enzymatic synthesis of benzocispentacin and its new six- and seven-membered homologues

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Abstract

A very efficient enzymatic method was developed for the synthesis of new enantiomeric benzocispentacin and its six- and seven-membered homologues through the Lipolase (lipase B from Candida antarctica) catalyzed enantioselective (E > 200) ring opening of 3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, 4,5-benzo-7-azabicyclo[4.2.0]octan-8-one, and 5,6-benzo-8-azabicyclo[5.2.0] nonan-9-one with H2O in iPr2O at 60°C. The (1R,2R)-β-amino acids (ee ≥ 96%, yields ≥ 40%) and (1S,6S)-, (1S,7S)-, and (1S,8S)-β-lactams (ee > 99%, yields ≥ 44%) produced could be easily separated. The ring opening of racemic and enantiomeric β-lactams with 18% HCl afforded the corresponding β-amino acid hydrochlorides.

Original languageEnglish
Pages (from-to)2587-2592
Number of pages6
JournalChemistry - A European Journal
Volume12
Issue number9
DOIs
Publication statusPublished - Mar 8 2006

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Keywords

  • Amino acids
  • Cleavage reactions
  • Enantioselectivity
  • Enzymes
  • Lactams

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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