• Regioselective and Enantiospecific Synthesis of Dioxepines by (Cyclopentadienyl)ruthenium-Catalyzed Condensations of Diazocarbonyls and Oxetanes
    Lo Egger, Laure Gune, Thomas Brgi and Jrme Lacour
    Advanced Synthesis & Catalysis, 359 (17) , 2017, p2918-2923
    Keywords: diazo compounds; insertion; metal carbenes; oxetanes; oxonium ylides; retention of configuration
    DOI:10.1002/adsc.201700638 | unige:96477 | Abstract | Article HTML | Article PDF
1,4-Dioxepines result from the decomposition of α-diazo-β-keto esters in the presence of oxetanes using the catalytic combination of the (cyclopentadienyl)ruthenium complex [CpRu(CH3CN)3][BArF] and 1,10-phenanthroline. The regioselective [4+3] insertions follow an SN1-like mechanism and occur yet enantiospecifically (es 74%). The retention of configuration was ascertained by vibrational circular dichroism (VCD) and solid state analyses. Furans, products of [4+1] insertions, are only observed as traces in the above protocol. To promote their formation under CpRu catalysis, it is necessary to use a two-step process with γ-halogenated alcohols as substrates.

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Brgi, Thomas Egger, Lo Gune, Laure Lacour, Jrme 
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