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Chemoenzymatic Asymmetric Synthesis of Pyridine-Based α-Fluorinated Secondary Alcohols |
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| Authors: | Dr Timo Broese Dr Peter Ehlers Dr Peter Langer Dr Jan von Langermann |
| Affiliation: | 1. Institute of Chemistry, Biocatalytic Synthesis Group, University of Rostock, Albert-Einstein-Str. 3?A, 18059 Rostock, Germany
Graforce GmbH, Johann-Hittorf-Str. 8, 12489 Berlin, Germany;2. Institute of Chemistry, Organic Chemistry, University of Rostock, Albert-Einstein-Str. 3?A, 18059 Rostock, Germany;3. Institute of Chemistry, Biocatalytic Synthesis Group, University of Rostock, Albert-Einstein-Str. 3?A, 18059 Rostock, Germany |
| Abstract: | Fluoro-substituted and heteroaromatic compounds are valuable intermediates for a variety of applications in pharma- and agrochemistry and synthetic chemistry. This study investigates the chemoenzymatic preparation of chiral alcohols bearing a heteroaromatic ring with an increasing degree of fluorination in α-position. Starting from readily available picoline derivatives prochiral α-halogenated acyl moieties were introduced with excellent selectivity and 64–95 % yield. The formed carbonyl group was subsequently reduced to the corresponding alcohols using the alcohol dehydrogenase from Lactobacillus kefir, yielding an enantiomeric excess of 95–>99 % and up to 98 % yield. |
| Keywords: | alcohol enzymes enantioselectivity fluorine heteroaromatic |