Lipase-catalyzed kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-acetic acid esters

Tihamér A. Paál, Eniko Forró, Ferenc Fülöp, Arto Liljeblad, Liisa T. Kanerva

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The enantiomers of 1,2,3,4-tetrahydroisoquinoline- and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetic acids were prepared via Burkholderia cepacia lipase (lipase PS-D)-catalyzed kinetic resolution of the corresponding ethyl and 2-methoxyethyl esters using enantioselective (E > 200) hydrolysis in DIPE. The (S)-acids were produced enzymatically, whereas the (R)-acids were obtained via the chemical hydrolysis of the unreacted (R)-esters. The solvent and its water content had major effects on both reactivity and enantioselectivity. The methoxyethyl moiety of the ester had a key role concerning the reactivity of the substrates.

Original languageEnglish
Pages (from-to)2784-2788
Number of pages5
JournalTetrahedron Asymmetry
Volume19
Issue number24
DOIs
Publication statusPublished - Dec 12 2008

ASJC Scopus subject areas

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

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