Lipase-catalyzed kinetic resolution of 2-aminocyclopentane- and 2-aminocyclohexanecarboxamides

Mónika Fitz, Katri Lundell, Ferenc Fülöp, Liisa T. Kanerva

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Candida antarctica lipase B (CAL-B)-catalyzed N-acylation with 2,2,2-trifluoroethyl butanoate in solvent mixtures of tert-butyl methyl ether and tert-amyl alcohol was used to prepare all the enantiomers of cis- and trans-2-aminocyclopentane- and -cyclohexanecarboxamides. An unexpected change in enantiopreference, accompanied by low enantioselectivity, was observed when Pseudomonas cepacia lipase (cis-cyclohexane substrate) or C. antarctica lipase A (cis-cyclopentane and -cyclohexane substrates) replaced CAL-B.

Original languageEnglish
Pages (from-to)1129-1134
Number of pages6
JournalTetrahedron Asymmetry
Volume17
Issue number7
DOIs
Publication statusPublished - Apr 3 2006

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ASJC Scopus subject areas

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

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