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

Hyseni M, Zumbrägel N, Offermanns H, Gröger H (2019)
Chemistry 2019(1): 180-191.

Zeitschriftenaufsatz | Veröffentlicht| Englisch
 
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Autor/in
Hyseni, Mentor; Zumbrägel, NadineUniBi ; Offermanns, Heribert; Gröger, HaraldUniBi
Abstract / Bemerkung
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
Stichworte
amines; β-aminothiols; Asinger chemistry; chemoenzymatic synthesis; heterocycles
Erscheinungsjahr
2019
Zeitschriftentitel
Chemistry
Band
2019
Ausgabe
1
Seite(n)
180-191
eISSN
2624-8549
Finanzierungs-Informationen
Article Processing Charge funded by the Deutsche Forschungsgemeinschaft and the Open Access Publication Fund of Bielefeld University.
Page URI
https://pub.uni-bielefeld.de/record/2938420

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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;2019(1):180-191.
Hyseni, M., Zumbrägel, N., Offermanns, H., & Gröger, H. (2019). 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. doi:10.3390/chemistry1010012
Hyseni, M., Zumbrägel, N., Offermanns, H., and Gröger, H. (2019). Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines. Chemistry 2019, 180-191.
Hyseni, M., et al., 2019. Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines. Chemistry, 2019(1), p 180-191.
M. Hyseni, et al., “Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines”, Chemistry, vol. 2019, 2019, pp. 180-191.
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, 180-191 (2019).
Hyseni, Mentor, Zumbrägel, Nadine, Offermanns, Heribert, and Gröger, Harald. “Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines”. Chemistry 2019.1 (2019): 180-191.
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2019-10-29T07:32:02Z
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