Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters

Beulshausen, Tessa; Groth, Ulrich; Schöllkopf, Ulrich

Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters

Dateien

Asymmetric_Synthesis_of_Diastereomerically_and_Enantiomerically_.pdfGröße: 434.11 KBDownloads: 270

Datum

1992

Autor:innen

Beulshausen, Tessa

Groth, Ulrich

Schöllkopf, Ulrich

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Liebigs Annalen der Chemie. 1992, 1992(5), pp. 523-526. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199219920190

Zusammenfassung

A novel method for the synthesis of N-methylserines has been developed. The oxazolidines 4 are formed by condensation of the serine methyl esters 1 with formaldehyde. These intermediates are subsequently reduced to the N-methylserine methyl esters 9 by an acid-catalyzed ring opening via their iminium ions 2 with triethylsilane/trifluoroacetic acid.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

Serine derivatives, Bislactim ether method

Zitieren

ISO 690

BEULSHAUSEN, Tessa, Ulrich GROTH, Ulrich SCHÖLLKOPF, 1992. Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters. In: Liebigs Annalen der Chemie. 1992, 1992(5), pp. 523-526. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199219920190

BibTex

@article{Beulshausen1992Asymm-9671,
  year={1992},
  doi={10.1002/jlac.199219920190},
  title={Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters},
  number={5},
  volume={1992},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={523--526},
  author={Beulshausen, Tessa and Groth, Ulrich and Schöllkopf, Ulrich}
}

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/123456789/9671">
    <dcterms:abstract xml:lang="deu">A novel method for the synthesis of N-methylserines has been developed. The oxazolidines 4 are formed by condensation of the serine methyl esters 1 with formaldehyde. These intermediates are subsequently reduced to the N-methylserine methyl esters 9 by an acid-catalyzed ring opening via their iminium ions 2 with triethylsilane/trifluoroacetic acid.</dcterms:abstract>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:contributor>Schöllkopf, Ulrich</dc:contributor>
    <dc:creator>Beulshausen, Tessa</dc:creator>
    <dc:creator>Groth, Ulrich</dc:creator>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9671/1/Asymmetric_Synthesis_of_Diastereomerically_and_Enantiomerically_.pdf"/>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/>
    <dc:contributor>Groth, Ulrich</dc:contributor>
    <dcterms:bibliographicCitation>First publ. in: Liebigs Annalen der Chemie 1992, 5, pp. 523-526</dcterms:bibliographicCitation>
    <dc:contributor>Beulshausen, Tessa</dc:contributor>
    <dc:creator>Schöllkopf, Ulrich</dc:creator>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9671"/>
    <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights>
    <dcterms:title>Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters</dcterms:title>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:13:35Z</dc:date>
    <dcterms:issued>1992</dcterms:issued>
    <dc:format>application/pdf</dc:format>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9671/1/Asymmetric_Synthesis_of_Diastereomerically_and_Enantiomerically_.pdf"/>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:13:35Z</dcterms:available>
    <dc:language>eng</dc:language>
  </rdf:Description>
</rdf:RDF>

Universitätsbibliographie

Nein