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

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Titel
Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines
Verfasser
Hyseni, Mentor ; Zumbrägel, Nadine ; Offermanns, Heribert ; Gröger, Harald
Enthalten in
Chemistry, Jg. 2019 H. 1, S. 180-191
Erschienen
2019
Sprache
Englisch
Dokumenttyp
Aufsatz in einer Zeitschrift
Schlagwörter
amines / β-aminothiols / Asinger chemistry / chemoenzymatic synthesis / heterocycles
URN
urn:nbn:de:0070-pub-29384200
DOI
10.3390/chemistry1010012

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Abstract

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

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