Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters

被引：24

作者：

Paal, Tihamer A. ^{[1
,2
]}

Liljeblad, Arto ^{[1
]}

Kanerva, Liisa T. ^{[1
]}

Forro, Eniko ^{[2
]}

Fueloep, Ferenc ^{[2
]}

机构：

[1] Univ Turku, Dept Pharmacol Drug Dev & Therapeut, Lab Synthet Drug Chem, Turku 20250, Finland

[2] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 31期

基金：

匈牙利科学研究基金会;

关键词：

Dynamic kinetic resolution; Enzyme catalysis; Nitrogen heterocycles;

D O I：

10.1002/ejoc.200800789

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of both enantiomers of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinotine-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-Tetrahydroisoquinotine-1-carboxylic acid was obtained with high enantiopurity (98%ee) and in good yield (85 %) in a CAL-B-catalysed process, under similar conditions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5269 / 5276

页数：8

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