Gadolinium triflate catalyzed alkylation of pyrroles: efficient synthesis of 3-oxo-2,3-dihydro-1H-pyrrolizine derivatives

ÜNALEROĞLU C., Yazici A.

TETRAHEDRON, cilt.63, sa.25, ss.5608-5613, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 25
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1016/j.tet.2007.04.018
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5608-5613
  • Hacettepe Üniversitesi Adresli: Evet

Özet

Novel 2-alkylated pyrrole derivatives were synthesized regioselectively by Gd(OTf)(3) catalyzed addition reactions of pyrrole to substituted dimethyl 2-benzylidenemalonate derivatives under mild reaction conditions. 2-Alkylated pyrrole derivatives are used for the construction of the 3-oxo pyrrolizine skeleton. Intramolecular cyclization of alkylated pyrrole derivatives afforded new diastereoselective 3-oxo-2,3-dihydro-1H-pyrrolizine derivatives with good to high yields. (C) 2007 Elsevier Ltd. All rights reserved.