dc.contributor.author
Brennecke, Benjamin
dc.contributor.author
Micó, Alicia Castello
dc.contributor.author
Selter, Lars
dc.contributor.author
Accorsi, Matteo
dc.contributor.author
Zimmer, Reinhold
dc.contributor.author
Reissig, Hans-Ulrich
dc.date.accessioned
2021-09-03T14:44:52Z
dc.date.available
2021-09-03T14:44:52Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/31827
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-31560
dc.description.abstract
The optimized coupling of N-protected (S)-proline and (2S,4R)-4-hydroxyproline derivatives with (Z)-4-aminopent-3-en-2-one provided the expected β-ketoenamides in good to excellent yields. The subsequent intramolecular cyclizations afforded enantiopure pyridin-4-one derivatives with pyrrolidin-2-yl substituents. The nonaflates generated from these intermediates were excellent precursors for typical palladium-catalyzed coupling reactions. Oxidation with m-chloroperbenzoic acid gave pyrrolidine N-oxides whose subsequent reactions were investigated. The condensation of β-ketoenamides with hydroxylamine hydrochloride furnished the corresponding enantiopure pyrimidine N-oxides in good yields. The subsequent Boekelheide rearrangement provided hydroxymethyl-substituted pyrimidine derivatives together with minor components. Overall, this study nicely demonstrates the potential of (S)-proline- or (2S,4R)-4-hydroxyproline-derived β-ketoenamides to approach a library of novel chiral pool-derived enantiopure functionalized pyridine and pyrimidine derivatives.
en
dc.format.extent
12 Seiten
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject
Cyclization of β-ketoenamides
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
A Proline and 4-Hydroxyproline Based Approach to Enantiopure Pyrrolidin-2-yl-Substituted Pyridine and Pyrimidine Derivatives
dc.type
Wissenschaftlicher Artikel
dcterms.bibliographicCitation.doi
10.1002/ejoc.202100887
dcterms.bibliographicCitation.journaltitle
European Journal of Organic Chemistry
dcterms.bibliographicCitation.number
33
dcterms.bibliographicCitation.pagestart
4750
dcterms.bibliographicCitation.pageend
4761
dcterms.bibliographicCitation.volume
2021
dcterms.bibliographicCitation.url
https://doi.org/10.1002/ejoc.202100887
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Chemie und Biochemie
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refubium.funding
DEAL Wiley
refubium.note.author
Die Publikation wurde aus Open Access Publikationsgeldern der Freien Universität Berlin gefördert.
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
1099-0690