Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids

Kurzanzeige
dc.contributor.authorGroth, Ulrich
dc.contributor.authorLehmann, Lutzdeu
dc.contributor.authorRichter, Lutzdeu
dc.contributor.authorSchöllkopf, Ulrichdeu
dc.date.accessioned2011-03-24T18:13:38Zdeu
dc.date.available2011-03-24T18:13:38Zdeu
dc.date.issued1993deu
dc.description.abstractThe lithium or potassium derivative of diethyl isocyanometh-ylphosphonate (1) reacts with epoxides in the presence of boron trifluoride-diethyl ether to provide the diethyl 3-hy-droxy-1-isocyanoalkylphosphonates rac-3. The corresponding mesylates rac-4 undergo a base-mediated cyclization to the diethyl 1-isocyanocyclopropylphosphonates rac-5. Acidic hydrolysis affords the diethyl l-aminocyanocyclopropylphos phonates roc-6, which upon treatment with trimethylsilyl iodide yield the 1-aminocyclopropylphosphonic acids rac-7. A base-mediated cycloalkylation of 1 with dibromoalkanes 10 gives the diethyl 1-isocyanocycloalkylphosphonates 11 which are suitable precursors for the achiral l-aminocycloal-kylphosphonic acids.eng
dc.description.versionpublished
dc.format.mimetypeapplication/pdfdeu
dc.identifier.citationFirst publ. in: Liebigs Annalen der Chemie 1993, 4, pp. 427-431deu
dc.identifier.doi10.1002/jlac.199319930169
dc.identifier.ppn276853571deu
dc.identifier.urihttp://kops.uni-konstanz.de/handle/123456789/9676
dc.language.isoengdeu
dc.legacy.dateIssued2008deu
dc.rightsAttribution-NonCommercial-NoDerivs 2.0 Generic
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/2.0/
dc.subjectAlpha-Aminophosphonic acidsdeu
dc.subjectCyclopropanationdeu
dc.subjectdiastereoselectivedeu
dc.subjectIsocyanidesdeu
dc.subject.ddc540deu
dc.titleSynthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acidseng
dc.typeJOURNAL_ARTICLEdeu
dspace.entity.typePublication
kops.citation.bibtex
@article{Groth1993Synth-9676,
  year={1993},
  doi={10.1002/jlac.199319930169},
  title={Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids},
  number={4},
  volume={1993},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={427--431},
  author={Groth, Ulrich and Lehmann, Lutz and Richter, Lutz and Schöllkopf, Ulrich}
}
kops.citation.iso690GROTH, Ulrich, Lutz LEHMANN, Lutz RICHTER, Ulrich SCHÖLLKOPF, 1993. Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids. In: Liebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169deu
kops.citation.iso690GROTH, Ulrich, Lutz LEHMANN, Lutz RICHTER, Ulrich SCHÖLLKOPF, 1993. Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids. In: Liebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169eng
kops.citation.rdf
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/9676">
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:title>Synthesis of Diastereomerically Pure 1-Aminocyclopropylphosphonic Acids</dcterms:title>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:13:38Z</dc:date>
    <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/>
    <dc:contributor>Lehmann, Lutz</dc:contributor>
    <dc:language>eng</dc:language>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9676/1/Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdf"/>
    <dc:format>application/pdf</dc:format>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:13:38Z</dcterms:available>
    <dcterms:abstract xml:lang="eng">The lithium or potassium derivative of diethyl isocyanometh-ylphosphonate (1) reacts with epoxides in the presence of boron trifluoride-diethyl ether to provide the diethyl 3-hy-droxy-1-isocyanoalkylphosphonates rac-3. The corresponding mesylates rac-4 undergo a base-mediated cyclization to the diethyl 1-isocyanocyclopropylphosphonates rac-5. Acidic hydrolysis affords the diethyl l-aminocyanocyclopropylphos phonates roc-6, which upon treatment with trimethylsilyl iodide yield the 1-aminocyclopropylphosphonic acids rac-7. A base-mediated cycloalkylation of 1 with dibromoalkanes 10 gives the diethyl 1-isocyanocycloalkylphosphonates 11 which are suitable precursors for the achiral l-aminocycloal-kylphosphonic acids.</dcterms:abstract>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9676/1/Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdf"/>
    <dc:creator>Groth, Ulrich</dc:creator>
    <dcterms:issued>1993</dcterms:issued>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9676"/>
    <dc:contributor>Schöllkopf, Ulrich</dc:contributor>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:creator>Richter, Lutz</dc:creator>
    <dc:creator>Schöllkopf, Ulrich</dc:creator>
    <dc:contributor>Groth, Ulrich</dc:contributor>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Lehmann, Lutz</dc:creator>
    <dc:contributor>Richter, Lutz</dc:contributor>
    <dcterms:bibliographicCitation>First publ. in: Liebigs Annalen der Chemie 1993, 4, pp. 427-431</dcterms:bibliographicCitation>
  </rdf:Description>
</rdf:RDF>
kops.description.openAccessopenaccessgreen
kops.flag.knbibliographyfalse
kops.identifier.nbnurn:nbn:de:bsz:352-opus-47196deu
kops.opus.id4719deu
kops.sourcefieldLiebigs Annalen der Chemie. 1993, <b>1993</b>(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169deu
kops.sourcefield.plainLiebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169deu
kops.sourcefield.plainLiebigs Annalen der Chemie. 1993, 1993(4), pp. 427-431. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199319930169eng
relation.isAuthorOfPublication8c7e9e13-9b97-4d86-a4d8-dfb6aa62420b
relation.isAuthorOfPublication.latestForDiscovery8c7e9e13-9b97-4d86-a4d8-dfb6aa62420b
source.bibliographicInfo.fromPage427
source.bibliographicInfo.issue4
source.bibliographicInfo.toPage431
source.bibliographicInfo.volume1993
source.identifier.eissn1099-0690
source.identifier.issn0170-2041
source.periodicalTitleLiebigs Annalen der Chemie

Dateien

Originalbündel

Gerade angezeigt 1 - 1 von 1
Vorschaubild nicht verfügbar
Name:
Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdf
Größe:
624.29 KB
Format:
Adobe Portable Document Format
Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdf
Synthesis_of_Diastereomerically_Pure_1_Aminocyclopropylphosphonic_Acids.pdfGröße: 624.29 KBDownloads: 423

Sammlungen

Chemie: Publikationen