Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

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

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A dynamic kinetic resolution method for the preparation of enantiopure 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (R)-2 was developed involving the CAL-B-catalyzed enantioselective hydrolysis of the corresponding ethyl ester (±)-1 in toluene/acetonitrile (4:1) containing 1 equiv of added water and 0.25 equiv of dipropylamine. This method allowed the preparation of (R)-2 (ee = 96%) with 80% isolated yield. The kinetic resolution of (±)-1 in diisopropyl ether at 3 °C afforded both enantiomers with ee ≥92%.

Original languageEnglish
Pages (from-to)1428-1433
Number of pages6
JournalTetrahedron Asymmetry
Volume18
Issue number12
DOIs
Publication statusPublished - Jul 4 2007

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid'. Together they form a unique fingerprint.

  • Cite this