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Enantioselective Synthesis of Thiomorpholines through Biocatalytic Reduction of 3,6-Dihydro-2 H -1,4-thiazines Using Imine Reductases.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Sep 02; Vol. 87 (17), pp. 11369-11378. Date of Electronic Publication: 2022 Aug 15. - Publication Year :
- 2022
-
Abstract
- In this work, an enantioselective biocatalytic synthesis of chiral thiomorpholines using imine reductases (IREDs) is described. As substrates, four prochiral and one chiral 3,6-dihydro-2 H -1,4-thiazines were synthesized in a modified Asinger reaction and subsequently reduced using imine reductases as a biocatalyst, NADPH as a cofactor, and a glucose dehydrogenase (GDH)-glucose cofactor regeneration system. As a result, chiral thiomorpholines with a stereogenic center created in 3-position were obtained under mild process conditions with high conversions and excellent enantioselectivities of up to 99%. Furthermore, as a proof of concept, a sequential one-pot process combining both individual reaction steps was achieved.
- Subjects :
- Imines
Morpholines
Stereoisomerism
Oxidoreductases
Thiazines
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35969670
- Full Text :
- https://doi.org/10.1021/acs.joc.2c00839