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J Biotechnol. 2019 Feb 10;291:35-40. doi: 10.1016/j.jbiotec.2018.12.009. Epub 2018 Dec 20.

One-pot synthesis of a 3-thiazolidine through combination of an Asinger-type multi-component-condensation reaction with an enzymatic imine reduction.

Author information

1
Chair of Organic Chemistry I, Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany.
2
Chair of Organic Chemistry I, Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany. Electronic address: harald.groeger@uni-bielefeld.de.

Abstract

Addressing the combination of heterocyclic chemistry and biocatalysis, a one-pot synthesis of a 3-thiazolidine by means of an initial Asinger-type multi-component-condensation reaction under formation of a 3-thiazoline and a subsequent enzymatic reduction of this cyclic imine is reported. The one-pot process is conducted in a sequential mode and without the need for a spatial compartmentalization of the single reaction steps. For the biocatalytic reduction an imine reductase was used in combination with a glucose dehydrogenase and D-glucose for in situ-cofactor recycling. This process has been applied successfully towards the synthesis of (S)-2,2,3-trimethyl-1-thia-4-azaspiro[4.4]nonane on a 4.5 mmol scale leading to moderate conversion and excellent enantioselectivity of 99% enantiomeric excess.

KEYWORDS:

Asinger-type multi-component-condensation reaction; Asymmetric synthesis; Biocatalysis; Cascades; Heterocycles; One-pot processes

PMID:
30579889
DOI:
10.1016/j.jbiotec.2018.12.009
[Indexed for MEDLINE]

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