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

Paál Tihamér A. | Zendy; Liljeblad Arto | Zendy; Kanerva Liisa T. | Zendy; Forró Enikő | Zendy; Fülöp Ferenc | Zendy

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

Author(s) -

Paál Tihamér A.,

Liljeblad Arto,

Kanerva Liisa T.,

Forró Enikő,

Fülöp Ferenc

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800789

Subject(s) - chemistry , tetrahydroisoquinoline , kinetic resolution , enantioselective synthesis , hydrolysis , enantiomer , carboxylic acid , biocatalysis , yield (engineering) , enantiomeric excess , enzymatic hydrolysis , aqueous solution , stereochemistry , organic chemistry , medicinal chemistry , catalysis , reaction mechanism , materials science , metallurgy

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 NH 4 OAc 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, 69451 Weinheim, Germany, 2008)

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