22422-31-7Relevant academic research and scientific papers
Regioselective and Enantiospecific Synthesis of Dioxepines by (Cyclopentadienyl)ruthenium-Catalyzed Condensations of Diazocarbonyls and Oxetanes
Egger, Léo,Guénée, Laure,Bürgi, Thomas,Lacour, Jér?me
, p. 2918 - 2923 (2017)
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. (Figure presented.).
