Copper-Catalyzed Bis(methoxycarbonyl)carbene Reactions of alpha,beta-Unsaturated Carboxamides


Merey G., Anaç O.

HELVETICA CHIMICA ACTA, vol.94, no.6, pp.1053-1064, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 94 Issue: 6
  • Publication Date: 2011
  • Doi Number: 10.1002/hlca.201000384
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1053-1064
  • Istanbul Technical University Affiliated: Yes

Abstract

The [Cu(acac)(2)]-catalyzed reactions of alpha,beta-unsaturated carboxamides with dimethyl diazomalonate yielded dihydrofuran derivatives by a 1,5-electrocyclic reaction at C(beta), and butadiene derivatives by carbene addition reaction at C(alpha) (Schemes 4 and 5; Table). Phenyl substituents at the N-atom of the amides seem to be effective on the reaction pathways (Table).