An effective approach to the enantiomers of alicyclic β-aminonitriles by using lipase catalysis

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Lipase-catalyzed N-acylations of racemic cis- and trans-2- aminocyclopentane- (and cyclohexane-) carbonitriles with 2,2,2-trifluoethyl butanoate in tert-butyl methyl ether (TBME) and in room-temperature ionic liquids (RTILs) were studied. The racemates were effectively resolved (E >200) on a preparative scale by lipase PS-C II (lipase from Burkholderia cepacia) in TBME, resulting in two enantiomers in their enantiopure forms at 50% conversion. The reactions in RTILs with Novozym 435 (Candida antarctica lipase B) were slow and proceeded with low enantioselectivity.

Original languageEnglish
Pages (from-to)3690-3697
Number of pages8
JournalTetrahedron Asymmetry
Volume16
Issue number22
DOIs
Publication statusPublished - Nov 14 2005

ASJC Scopus subject areas

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

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