| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345091 | Tetrahedron: Asymmetry | 2014 | 7 Pages |
A biocatalyzed reduction of a prochiral bicyclic ketone afforded enantiomerically pure (R)-2-acetylamino-6-hydroxy-4,5,6,7-tetrahydrobenzothiazole, a synthon of the anti-Parkinson (S)-pramipexole and its (R)-isomer, which is currently under investigation for the treatment of amyotrophic lateral sclerosis (ALS).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(R)-2-Acetylamino-6-hydroxy-4,5,6,7-tetrahydrobenzothiazoleC9H12N2O2S>98% ee (by HPLC)[α]D20 = +25.5 (c 1 CH3OH)Source of chirality: Saccharomyces cerevisiaeAbsolute configuration: (R)
(S)-2-Acetylamino-6-amino-4,5,6,7-tetrahydrobenzothiazoleC9H13N3OS>98% ee (by HPLC)[α]D20 = −59.1 (c 1 CH3OH)Source of chirality: Saccharomyces cerevisiaeAbsolute configuration: (S)
(S)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazoleC7H11N3S>98% ee (by HPLC)[α]D20 = −91.0 (c 1 CH3OH)Source of chirality: Saccharomyces cerevisiaeAbsolute configuration: (S)
