Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts

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Dündar E., Tanyeli C.

Tetrahedron Letters, cilt.73, ss.1-4, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.tetlet.2021.153153
  • Dergi Adı: Tetrahedron Letters
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, Veterinary Science Database
  • Sayfa Sayıları: ss.1-4
  • Anahtar Kelimeler: Asymmetric synthesis, Organocatalysis, Squaramide organocatalyst, Friedel-Crafts alkylation, Indole, MICHAEL ADDITION, DERIVATIVES, CATALYST
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

© 2021 Elsevier LtdA series of chiral bifunctional quinine and 2-aminoDMAP based squaramide organocatalysts are evaluated in Friedel-Crafts alkylation of indoles with nitroolefins. These 3-substituted indole derivatives are synthesized in the presence of sterically encumbered tert-butyl squaramide/quinine with high enantioselectivity (up to >99% ee) and moderate chemical yields (up to 80%) by representing as chiral precursors for very important biologically active molecules. Besides, this asymmetric transformation provides a very simple, efficient, clean and environmental friendly route. In addition, this process has very mild reaction conditions such as ambient temperature and usage of only 2 mol% catalyst loading compared to previous studies in literature.