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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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{
  "DOI": "10.1039/d1nj05121k", 
  "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.", 
  "author": [
    {
      "family": "Susam", 
      "given": " Zeynep Dilsad"
    }, 
    {
      "family": "Bozdemir", 
      "given": " Merve"
    }, 
    {
      "family": "Gundogdu", 
      "given": " Gulsum"
    }, 
    {
      "family": "Tanyeli", 
      "given": " Cihangir"
    }
  ], 
  "container_title": "NEW JOURNAL OF CHEMISTRY", 
  "id": "233362", 
  "issue": "2", 
  "issued": {
    "date-parts": [
      [
        2022, 
        1, 
        1
      ]
    ]
  }, 
  "page": "599-606", 
  "title": "Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst", 
  "type": "article-journal", 
  "volume": "46"
}
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