Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters

[Image: see text] The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H(2)O(2). The reaction proceeds via in situ formation of a hyperval...

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Autores principales: Mairhofer, Christopher, Novacek, Johanna, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7418104/
https://www.ncbi.nlm.nih.gov/pubmed/32706973
http://dx.doi.org/10.1021/acs.orglett.0c02198
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author Mairhofer, Christopher
Novacek, Johanna
Waser, Mario
author_facet Mairhofer, Christopher
Novacek, Johanna
Waser, Mario
author_sort Mairhofer, Christopher
collection PubMed
description [Image: see text] The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H(2)O(2). The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent.
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spelling pubmed-74181042020-08-11 Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters Mairhofer, Christopher Novacek, Johanna Waser, Mario Org Lett [Image: see text] The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H(2)O(2). The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent. American Chemical Society 2020-07-24 2020-08-07 /pmc/articles/PMC7418104/ /pubmed/32706973 http://dx.doi.org/10.1021/acs.orglett.0c02198 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Mairhofer, Christopher
Novacek, Johanna
Waser, Mario
Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title_full Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title_fullStr Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title_full_unstemmed Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title_short Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters
title_sort synergistic ammonium (hypo)iodite/imine catalysis for the asymmetric α-hydroxylation of β-ketoesters
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7418104/
https://www.ncbi.nlm.nih.gov/pubmed/32706973
http://dx.doi.org/10.1021/acs.orglett.0c02198
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AT novacekjohanna synergisticammoniumhypoioditeiminecatalysisfortheasymmetricahydroxylationofbketoesters
AT wasermario synergisticammoniumhypoioditeiminecatalysisfortheasymmetricahydroxylationofbketoesters

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