NDLI: Biocatalytic access to nonracemic γ-oxo esters <i>via</i> stereoselective reduction using ene-reductases

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Green Chemistry Vol - 19 Issue - 1

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Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

Content Provider	Royal Society of Chemistry (RSC)
Author	Ruijter, Eelco Turrini, Nikolaus G. Niet, Daan J. H. van Orru, Romano V. A. Faber, Kurt Hall, Mélanie Cioc, Răzvan C.
Copyright Year	2017
Abstract	The asymmetric bioreduction of α,β-unsaturated γ-keto esters using ene-reductases from the Old Yellow Enzyme family proceeds with excellent stereoselectivity and high conversion levels, covering a broad range of acyclic and cyclic derivatives. Various strategies were employed to provide access to both enantiomers, which are versatile precursors of bioactive molecules. The regioselectivity of hydride addition on di-activated alkenes was elucidated by isotopic labeling experiments and showed strong preference for the keto moiety as activating/binding group as opposed to the ester. Finally, chemoenzymatic synthesis of (R)-2-(2-oxocyclohexyl)acetic acid was achieved in high ee on a preparative scale combining enzymatic reduction followed by ester hydrogenolysis.
Starting Page	511
Ending Page	518
Page Count	8
File Format	HTM / HTML PDF
ISSN	14639262
Volume Number	19
Issue Number	2
Journal	Green Chemistry
DOI	10.1039/c6gc02493a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Stereoselectivity Regioselectivity Hydride Isotopic labeling Ester Carboxylic acid Hydrogenolysis
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Pollution

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Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

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Biocatalytic access to nonracemic γ-oxo esters via stereoselective reduction using ene-reductases

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