Towards an asymmetric organocatalytic α-cyanation of β-ketoesters

This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alk...

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Autores principales: Chowdhury, Raghunath, Schörgenhumer, Johannes, Novacek, Johanna, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4366011/
https://www.ncbi.nlm.nih.gov/pubmed/25843983
http://dx.doi.org/10.1016/j.tetlet.2015.02.116
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author Chowdhury, Raghunath
Schörgenhumer, Johannes
Novacek, Johanna
Waser, Mario
author_facet Chowdhury, Raghunath
Schörgenhumer, Johannes
Novacek, Johanna
Waser, Mario
author_sort Chowdhury, Raghunath
collection PubMed
description This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions.
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spelling pubmed-43660112015-04-01 Towards an asymmetric organocatalytic α-cyanation of β-ketoesters Chowdhury, Raghunath Schörgenhumer, Johannes Novacek, Johanna Waser, Mario Tetrahedron Lett Article This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities up to er = 76:24 under operationally simple conditions. Elsevier 2015-04-01 /pmc/articles/PMC4366011/ /pubmed/25843983 http://dx.doi.org/10.1016/j.tetlet.2015.02.116 Text en © 2015 The Authors http://creativecommons.org/licenses/by/4.0/ This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chowdhury, Raghunath
Schörgenhumer, Johannes
Novacek, Johanna
Waser, Mario
Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title_full Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title_fullStr Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title_full_unstemmed Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title_short Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
title_sort towards an asymmetric organocatalytic α-cyanation of β-ketoesters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4366011/
https://www.ncbi.nlm.nih.gov/pubmed/25843983
http://dx.doi.org/10.1016/j.tetlet.2015.02.116
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