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


Creative Commons License

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

NEW JOURNAL OF CHEMISTRY, vol.46, no.2, pp.599-606, 2022 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 46 Issue: 2
  • Publication Date: 2022
  • Doi Number: 10.1039/d1nj05121k
  • Journal Name: NEW JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chimica, EMBASE, DIALNET
  • Page Numbers: pp.599-606

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.