Chemoselective Carbenoid Reactions of Furan/Thiophene/Pyrrole Ring Containing Carbonyl and Conjugated Carbonyl at Their 2-Positions

Güngör F. Ş., Merey G., Anaç O.

ChemistrySelect, cilt.5, sa.17, ss.5337-5340, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 5 Sayı: 17
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/slct.202000584
  • Dergi Adı: ChemistrySelect
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Sayfa Sayıları: ss.5337-5340
  • Anahtar Kelimeler: carbenes, carbenoids, diazo compounds, hetaryl, oxo-polyene, HIGHLY ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC 4+1 CYCLOADDITIONS, C-H FUNCTIONALIZATION, YLIDE REACTIONS, DIAZO-COMPOUNDS, COPPER, DIHYDROFURANS, CYCLOPROPANATION, HETEROCYCLES, ENAMINONES
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimSeveral furyl/thiophenyl/N-methylpyrrolyl cores having aldehyde/ketone/ene-biscarbonyl/diene-biscarbonyl functions at their 2-positions were reacted with diazocarbonyl compounds in the presence of metal catalysts. Between the two possible reaction pathways which may take place either on the 2-substituent of hetaryl or on the core structure, only one of them was dominant for each reaction depending on substituents. Accordingly, in the reaction of thiophene-2-carbaldehyde with diazo compounds we obtained epoxy derivatives. On the other hand, dimethyl diazomalonate and furyl-ene-diketo/N-methylpyrrolyl-ene-diester yielded only novel dihydrofuran derivatives via [1,5]-electrocyclic ring closure. However, the reactions of 2-ene/diene-diester functionalized furans with dimethyl diazomalonate resulted polymethoxycarboxylate-substituted oxo-polyenes chemo-specifically in good yields.