Dynamic kinetic resolution of ethyl 1,2,3,4-tetrahydro-β-carboline-1-carboxylate Use of different hydrolases for stereocomplementary processes /
Both enantiomers of 1,2,3,4-tetrahydro- -carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98 % ee and 90 % yield in 20 min....
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2017
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| Sorozat: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
2017 No. 32 |
| doi: | 10.1002/ejoc.201700571 |
| mtmt: | 3262435 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/14932 |
| Tartalmi kivonat: | Both enantiomers of 1,2,3,4-tetrahydro- -carboline-1-carboxylic acid have been prepared by dynamic kinetic resolution of the corresponding ethyl ester (±)-1. CAL-B-catalysed hydrolysis of (±)-1·HCl in NH4OAc buffer (pH 8.0, 30 °C) provided amino acid (R)-2·HCl with 98 % ee and 90 % yield in 20 min. The hydrolysis with Alcalase in borate buffer (pH 8.0, 30 °C) showed S selectivity and the product (S)-2·HCl was obtained with 60 % ee and 66 % yield in 45 h. The absolute configuration of (S)-2 was determined by TDDFT electronic circular dichroism and optical rotation calculations. |
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| Terjedelem/Fizikai jellemzők: | 4713-4718 |
| ISSN: | 1434-193X |