Metal triflates-catalyzed conjugate addition of homochiral Pyrroles to alpha,beta-unsaturated esters


Unaleroglu C., Temelli B., Demir A. s.

SYNTHESIS-STUTTGART, no.15, pp.2574-2578, 2004 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2004
  • Doi Number: 10.1055/s-2004-831195
  • Journal Name: SYNTHESIS-STUTTGART
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.2574-2578
  • Keywords: homochiral pyrroles, metal triflates, conjugate addition, Friedel-Crafts reaction, pyrroles, INTRAMOLECULAR CARBENOID REACTIONS, DERIVATIVES, ALKYLATION, KETOESTERS

Abstract

The Friedel-Crafts reaction of homochiral pyrrole derivatives with alpha,beta-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectively at C-5 of pyrrole. The diastereoisomers were separated by column chromatography.