Co2(CO)8-induced domino reactions of ethyl diazoacetate, carbon monoxide and ferrocenylimines leading to 2-(1-ferrocenyl-methylidene)-malonic acid derivatives

János Balogh, Tamás Kégl, Ferenc Ungváry, Rita Skoda-Földes

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Novel 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained upon reacting ethyl diazoacetate, carbon monoxide and ferrocenylimines in the presence of Co2(CO)8 as catalyst under mild conditions. Presumably, the reaction involves three steps taking place in a domino fashion, (i) carbonylation of ethyl diazoacetate leading to a ketene derivative, (ii) [2+2] cycloaddition of the ketene with the ferrocenylimine present in the reaction mixture resulting in the formation of a β-lactam and (iii) N(1)-C(4) cleavage of the β-lactam ring. In most cases, 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained as a separable mixture of E- and Z-isomers in ratios depending on the structure of the imine component.

Original languageEnglish
Pages (from-to)4727-4730
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number33
DOIs
Publication statusPublished - 18 Aug 2009
Externally publishedYes

Fingerprint

Lactams
Carbon Monoxide
Derivatives
Imines
Cycloaddition Reaction
Carbonylation
Cycloaddition
Isomers
Catalysts
malonic acid
diazoacetic ester
ketene

Keywords

  • β-Lactams
  • Carbonylation
  • Cobalt-catalysis
  • Domino reactions

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Co2(CO)8-induced domino reactions of ethyl diazoacetate, carbon monoxide and ferrocenylimines leading to 2-(1-ferrocenyl-methylidene)-malonic acid derivatives. / Balogh, János; Kégl, Tamás; Ungváry, Ferenc; Skoda-Földes, Rita.

In: Tetrahedron Letters, Vol. 50, No. 33, 18.08.2009, p. 4727-4730.

Research output: Contribution to journalArticle

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AB - Novel 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained upon reacting ethyl diazoacetate, carbon monoxide and ferrocenylimines in the presence of Co2(CO)8 as catalyst under mild conditions. Presumably, the reaction involves three steps taking place in a domino fashion, (i) carbonylation of ethyl diazoacetate leading to a ketene derivative, (ii) [2+2] cycloaddition of the ketene with the ferrocenylimine present in the reaction mixture resulting in the formation of a β-lactam and (iii) N(1)-C(4) cleavage of the β-lactam ring. In most cases, 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained as a separable mixture of E- and Z-isomers in ratios depending on the structure of the imine component.

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