[CpRu]‐Catalyzed Carbene Insertions into Epoxides: 1,4‐Dioxene Synthesis through SN1‐Like Chemistry with Retention of Configuration |
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| Authors: | Dr. Thierry Achard Cecilia Tortoreto Dr. Amalia I. Poblador‐Bahamonde Dr. Laure Guénée Prof. Thomas Bürgi Prof. Jérôme Lacour |
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| Affiliation: | 1. Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4 (Switzerland) http://www.unige.ch/sciences/chiorg/lacour/;2. Laboratory of Crystallography, University of Geneva, Quai Ernest Ansermet 24, 1211 Geneva 4 (Switzerland);3. Department of Physical Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4 (Switzerland) |
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| 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. |
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| Keywords: | carbenes diazo compounds ruthenium stereoselectivity ylides |
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