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Regioselective and Enantiospecific Synthesis of Dioxepines by (Cyclopentadienyl)ruthenium-Catalyzed Condensations of Diazocarbonyls and Oxetanes

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Published in Advanced Synthesis and Catalysis. 2017, vol. 359, no. 17, p. 2918-2923
Abstract 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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Other version: http://doi.wiley.com/10.1002/adsc.201700638
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Research group Groupe Lacour
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EGGER, Leo et al. Regioselective and Enantiospecific Synthesis of Dioxepines by (Cyclopentadienyl)ruthenium-Catalyzed Condensations of Diazocarbonyls and Oxetanes. In: Advanced Synthesis and Catalysis, 2017, vol. 359, n° 17, p. 2918-2923. https://archive-ouverte.unige.ch/unige:96477

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Deposited on : 2017-09-04

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