TY  - JOUR
AB  - 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
DA  - 2019
DO  - 10.3390/chemistry1010012
KW  - amines
KW  - β-aminothiols
KW  - Asinger chemistry
KW  - chemoenzymatic synthesis
KW  - heterocycles
LA  - eng
IS  - 1
M2  - 180
PY  - 2019
SP  - 180-191
T2  - Chemistry
TI  - Expanding the Scope of Asinger Chemistry towards Enantiomerically Pure Secondary Amines and β-Aminothiols through Chemoenzymatic Derivatization of 3-Thiazolines
UR  - https://nbn-resolving.org/urn:nbn:de:0070-pub-29384200
Y2  - 2024-11-22T16:39:21
ER  -