Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines

Anac O., Sezer Ö., Candan O., Güngör F. Ş., Cansever M. S.

Tetrahedron Letters, vol.49, no.6, pp.1062-1065, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 49 Issue: 6
  • Publication Date: 2008
  • Doi Number: 10.1016/j.tetlet.2007.11.197
  • Journal Name: Tetrahedron Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1062-1065
  • Keywords: carbene, 1,5-electrocyclization, 1,7-electrocyclization, dihydrofuran, dihydrobenzoxepine, DIMETHYL DIAZOMALONATE, DIAZO-COMPOUNDS, RING-CLOSURE, CYCLOPROPANATION, CYCLIZATION, ALPHA,BETA-ENONES, ENAMINONES, EFFICIENT, ROUTE, CORE
  • Istanbul Technical University Affiliated: Yes

Abstract

α-Benzylidene-β,β′-biscarbonyl compounds were reacted with dimethyl diazomalonate using Cu(II) acetylacetonate as a catalyst. Dihydrofurans or mixtures of dihydrofurans and dihydrobenzoxepines were obtained depending on the nature of the carbonyl group present in the starting material. © 2007 Elsevier Ltd. All rights reserved.