Original Reactivity of α-Diazo-β-ketoesters Catalyzed by CpRu Complexes

Cecilia Tortoreto; Thierry Achard; Martina Austeri; Walid Zeghida; Jérôme Lacour

doi:10.2533/chimia.2014.243

Original Reactivity of α-Diazo-β-ketoesters Catalyzed by CpRu Complexes

Authors

Cecilia Tortoreto University of Geneva Department of Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva, Switzerland
Thierry Achard University of Geneva Department of Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva, Switzerland
Martina Austeri University of Geneva Department of Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva, Switzerland
Walid Zeghida University of Geneva Department of Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva, Switzerland
Jérôme Lacour University of Geneva Department of Chemistry Quai Ernest Ansermet 30 CH-1211 Geneva, Switzerland. jerome.lacour@unige.ch

DOI:

https://doi.org/10.2533/chimia.2014.243

Keywords:

Diazo compounds, Insertions, Metal carbenes, Oxonium ylide

Abstract

Using α-diazo-β-ketoesters as reagents and combinations of CpRu fragments and diimine ligands as catalysts, a series of original transformations have been obtained that can be rationalized by the formation of metal carbenes and metal-bound ylide intermediates. Interesting 1,3-dioxole, enol-acetal and 1,4-dioxene motifs are obtained directly when the reactive mixture is reacted in presence of aldehydes or ketones, THF and epoxides.