151004-93-2Relevant articles and documents
Directed (R)- or (S)-selective dynamic kinetic enzymatic hydrolysis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters
Paal, Tihamer A.,Liljeblad, Arto,Kanerva, Liisa T.,Forro, Eniko,Fueloep, Ferenc
, p. 5269 - 5276 (2008)
The first synthesis of both enantiomers of 6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline-1-carboxylic acid was accomplished through dynamic kinetic resolution in procedures based on CAL-B- or subtilisin Carlsberg-catalysed enantioselective hydrolysis of the corresponding ethyl esters in aqueous NH4OAc buffer at pH 8.5. The products were obtained with high enantiopurity (92-93%ee) in good yields (85-92%). (R)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid was obtained with high enantiopurity (98%ee) and in good yield (85%) in a CAL-B-catalysed process, under similar conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid
Paal, Tihamer A.,Forro, Eniko,Liljeblad, Arto,Kanerva, Liisa T.,Fueloep, Ferenc
, p. 1428 - 1433 (2008/02/10)
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%.