Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters

Szilvia Gedey, Arto Liljeblad, László Lázár, Ferenc Fülöp, Liisa T. Kanerva

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method.

Original languageEnglish
Pages (from-to)565-570
Number of pages6
JournalCanadian Journal of Chemistry
Volume80
Issue number6
DOIs
Publication statusPublished - Sep 18 2002

    Fingerprint

Keywords

  • Acylation
  • Alcoholysis
  • Interesterification
  • Lipase
  • Resolution
  • β-amino esters

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this