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

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Susam Z. D., Bozdemir M., Gundogdu G., Tanyeli C.

NEW JOURNAL OF CHEMISTRY, cilt.46, sa.2, ss.599-606, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 2
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1039/d1nj05121k
  • Dergi Adı: NEW JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chimica, EMBASE, DIALNET
  • Sayfa Sayıları: ss.599-606
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

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.