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

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Published in Angewandte Chemie: International Edition. 2014, vol. 53, no. 24, p. 6140-6144
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 CarbenesDiazo compoundsRutheniumStereoselectivityYlides
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Other version: http://doi.wiley.com/10.1002/anie.201402994
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ACHARD, Thierry et al. [CpRu]-Catalyzed Carbene Insertions into Epoxides: 1,4-Dioxene Synthesis through SN1-Like Chemistry with Retention of Configuration. In: Angewandte Chemie: International Edition, 2014, vol. 53, n° 24, p. 6140-6144. https://archive-ouverte.unige.ch/unige:37229

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Deposited on : 2014-06-10

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