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Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst

Susam, Zeynep Dilsad; Bozdemir, Merve; Gundogdu, Gulsum; Tanyeli, Cihangir


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/233362</identifier>
  <creators>
    <creator>
      <creatorName>Susam, Zeynep Dilsad</creatorName>
      <givenName>Zeynep Dilsad</givenName>
      <familyName>Susam</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Bozdemir, Merve</creatorName>
      <givenName>Merve</givenName>
      <familyName>Bozdemir</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Gundogdu, Gulsum</creatorName>
      <givenName>Gulsum</givenName>
      <familyName>Gundogdu</familyName>
      <affiliation>Turkish German Univ, Fac Sci, Dept Energy Sci &amp; Technol, TR-34820 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Tanyeli, Cihangir</creatorName>
      <givenName>Cihangir</givenName>
      <familyName>Tanyeli</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Enantioselective Synthesis Of 2,3-Dihydrofurans Using A Bifunctional Quinine/Squaramide Organocatalyst</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2022</publicationYear>
  <dates>
    <date dateType="Issued">2022-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/233362</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1039/d1nj05121k</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">Asymmetric organocatalytic domino type Michael-S(N)2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of alpha-bromonitroalkenes and 1,3-dicarbonyl compounds were allowed to react under optimized conditions, in the presence of a bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalyst. The conditions developed in this article have great advantages over the methods known in the literature in terms of reaction duration (1-6 h vs. 24-96 h) and reaction temperature (room temperature vs. -20 degrees C to -50 degrees C) giving rise to quite diastereoselective products with good enantioselectivities up to 97% ee.</description>
  </descriptions>
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