Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade

Handle URI:
http://hdl.handle.net/10754/625568
Title:
Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade
Authors:
El-Sepelgy, Osama ( 0000-0003-3131-4988 ) ; Brzozowska, Aleksandra; Rueping, Magnus ( 0000-0003-4580-5227 )
Abstract:
A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation-dehydrogenation-hydrogenation of prochiral ketones. By merging the iron-catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones, as well as diketones, were reductively acylated. The corresponding products were isolated with high yields and enantioselectivities. The use of an iron catalyst together with molecular hydrogen as the hydrogen donor and readily available ethyl acetate as acyl donor make this cascade process highly interesting in terms of both economic value and environmental credentials.
KAUST Department:
KAUST Catalysis Center (KCC)
Citation:
El-Sepelgy O, Brzozowska A, Rueping M (2017) Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade. ChemSusChem 10: 1664–1668. Available: http://dx.doi.org/10.1002/cssc.201700169.
Publisher:
Wiley-Blackwell
Journal:
ChemSusChem
Issue Date:
28-Feb-2017
DOI:
10.1002/cssc.201700169
Type:
Article
ISSN:
1864-5631
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/cssc.201700169/full
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorEl-Sepelgy, Osamaen
dc.contributor.authorBrzozowska, Aleksandraen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2017-10-03T12:49:26Z-
dc.date.available2017-10-03T12:49:26Z-
dc.date.issued2017-02-28en
dc.identifier.citationEl-Sepelgy O, Brzozowska A, Rueping M (2017) Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade. ChemSusChem 10: 1664–1668. Available: http://dx.doi.org/10.1002/cssc.201700169.en
dc.identifier.issn1864-5631en
dc.identifier.doi10.1002/cssc.201700169en
dc.identifier.urihttp://hdl.handle.net/10754/625568-
dc.description.abstractA general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation-dehydrogenation-hydrogenation of prochiral ketones. By merging the iron-catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones, as well as diketones, were reductively acylated. The corresponding products were isolated with high yields and enantioselectivities. The use of an iron catalyst together with molecular hydrogen as the hydrogen donor and readily available ethyl acetate as acyl donor make this cascade process highly interesting in terms of both economic value and environmental credentials.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/cssc.201700169/fullen
dc.subjectcascade catalysisen
dc.subjectchiral alcoholsen
dc.subjectenzymeen
dc.subjectkinetic resolutionen
dc.subjectracemizationen
dc.titleAsymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascadeen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalChemSusChemen
dc.contributor.institutionInstitute of Organic Chemistry; RWTH Aachen University; Landoltweg 1 52074 Aachen Germanyen
kaust.authorRueping, Magnusen
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