Asymmetric Synthesis of Trifluoromethyl Substituted Spiro[Indoline-3,4′-Pyrano[2,3-c]Pyrazole] Derivatives with Organocatalysts

Ozcan B. D., BAYER KÖMÜŞDOĞAN E., ŞAHİN E., TANYELİ C.

CHEMISTRYSELECT, cilt.9, sa.5, 2024 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 9 Sayı: 5
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1002/slct.202304275
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Atatürk Üniversitesi Adresli: Evet

Özet

Spirocyclic compounds have always attracted attention due to their presence as a structural core in a wide variety of natural and bioactive molecules and to exhibit pharmaceutical properties. An asymmetric synthesis of spiro[indoline-3,4 '-pyrano[2,3-c]pyrazoles] via Michael addition of trifluoromethyl substituted pyrazolone to isatylidene ethyl cyanoacetate derivatives was conducted with excellent enantioselectivities up to 99 % and up to 97 % isolated yield at room temperature with using 2 mol % of bifunctional quinine derived squaramide organocatalysts. Step into the intriguing world of enantiopure spirooxindoles: Bifunctional organocatalyst (see Picture) facilitates a highly enantioselective Michael addition of trifluoromethyl-substituted pyrazolone to isatylidene ethyl cyanoacetate derivatives at ambient temperature. image