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Publication 185  

  1. Regioselective and Enantiospecific Synthesis of Dioxepines by (Cyclopentadienyl)ruthenium-Catalyzed Condensations of Diazocarbonyls and Oxetanes
    Léo Egger, Laure Guénée, Thomas Bürgi, Jérôme Lacour
    Adv. Synth. Catal. 2017, 359, 2918-2923

1,4-Dioxepines result from the decomposition of α-diazo-β-ketoesters in the presence of oxetanes using, as catalyst, a combination of [CpRu(CH3CN)3][BArF] and 1,10-phenanthroline. The regioselective [4+3] insertions follow a SN1-like mechanism and occur yet enantiospecifically (es 74%). The retention of configuration was ascertained by 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

DOI: 10.1002/adsc.201700638 

open archive unige:96477