Efficient Catalytic Corey-Chaykovsky Reactions Involving Ketone Substrates

It has been demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal‐free methodology is of broad scope – both aliphatic and aromatic ketones (including trifluoro...

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Veröffentlicht in:Advanced synthesis & catalysis 2010-10, Vol.352 (11-12), p.2089-2093
Hauptverfasser: Kavanagh, Sarah A., Piccinini, Alessandro, Connon, Stephen J.
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Sprache:eng
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Zusammenfassung:It has been demonstrated for the first time that a sulfide catalyst, utilised at 20 mol% loading, can promote methylene transfer to ketones in the presence of methyl triflate and an organic base. This metal‐free methodology is of broad scope – both aliphatic and aromatic ketones (including trifluoromethyl ketones) can be converted to synthetically useful terminal epoxides in excellent yields at room temperature.
ISSN:1615-4150
1615-4169
1615-4169
DOI:10.1002/adsc.201000255