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

• Published in: Tetrahedron: asymmetry Vol. 18; no. 12; pp. 1428 - 1433
• Main Authors: Paál, Tihamér A., Forró, Enikő, Liljeblad, Arto, Kanerva, Liisa T., Fülöp, Ferenc
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.07.2007; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; Physical Sciences; Science & Technology; RACEMIZATION; ACYLATION; ANALOGS; ESTERS
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/j.tetasy.2007.05.016

Kinetic (KR) and dynamic kinetic resolution (DKR) of (±)- 1 has been performed through hydrolysis in organic solvents in the presence of Candida antarctica lipase B. 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%.