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Scientific article
English

[CpRu]-Catalyzed Carbene Insertions into Epoxides: 1,4-Dioxene Synthesis through SN1-Like Chemistry with Retention of Configuration

Published inAngewandte Chemie, vol. 53, no. 24, p. 6140-6144
Publication date2014
Abstract

Rather than lead to the usual deoxygenation pathway, metal carbenes derived from α-diazo-β-ketoesters undergo three-atom insertions into epoxides using a combination of 1,10-phenanthroline and [CpRu(CH3CN)3][BArF] as the catalyst. Original 1,4-dioxene motifs are obtained as single regio- and stereoisomers. A perfect syn stereochemistry (retention, e.r. up to 97:3) is observed for the ring opening, which behaves as an SN1-like transformation.

Keywords
  • Carbenes
  • Diazo compounds
  • Ruthenium
  • Stereoselectivity
  • Ylides
Citation (ISO format)
ACHARD, Thierry et al. [CpRu]-Catalyzed Carbene Insertions into Epoxides: 1,4-Dioxene Synthesis through S<sub>N</sub>1-Like Chemistry with Retention of Configuration. In: Angewandte Chemie, 2014, vol. 53, n° 24, p. 6140–6144. doi: 10.1002/anie.201402994
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ISSN of the journal1433-7851
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Creation06/06/2014 1:30:00 PM
First validation06/06/2014 1:30:00 PM
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