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Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines

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Chair of Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany
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Grünaustraße 2, 63457 Hanau, Germany
3
Former affiliation: Degussa-Hüls AG, Weißfrauenstraße 9, 60287 Frankfurt am Main, Germany
*
Author to whom correspondence should be addressed.
Chemistry 2019, 1(1), 180-191; https://doi.org/10.3390/chemistry1010012
Received: 21 August 2019 / Revised: 1 October 2019 / Accepted: 18 October 2019 / Published: 28 October 2019
(This article belongs to the Section Molecular Organic)
A proof of concept for a novel approach towards enantiomerically highly enriched acyclic secondary amines and β-aminothiols as non-cyclic target molecules when starting from 3-thiazolines as heterocycles is presented. Starting from 2,2,4,5,5-pentamethyl-3-thiazoline, we demonstrated this chemoenzymatic pathway to both of these types of amine molecules, which were isolated as urea derivatives with a non-optimized yield of up to 20%. As a substrate, 2,2,4,5,5-pentamethyl-3-thiazolidine, which was obtained with an enantiomeric excess (ee) of 99% in a biotransformation from the corresponding 3-thiazoline according to a recently developed protocol, was used. For the reductive desulfurization of this substrate leading to a sulfur-free secondary amine, in situ formed Ni2B turned out to be a suitable reducing reagent. However, when using lithium aluminum hydride as a reducing agent, β-aminothiol was obtained. View Full-Text
Keywords: amines; β-aminothiols; Asinger chemistry; chemoenzymatic synthesis; heterocycles amines; β-aminothiols; Asinger chemistry; chemoenzymatic synthesis; heterocycles
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Hyseni, M.; Zumbrägel, N.; Offermanns, H.; Gröger, H. Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines. Chemistry 2019, 1, 180-191.

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