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


TETRAHEDRON, vol.63, no.25, pp.5608-5613, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 25
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2007.04.018
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5608-5613
  • Hacettepe University Affiliated: Yes


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.