Efficient Catalytic Corey–Chaykovsky Reactions Involving Ketone Substrates

SA Kavanagh, A Piccinini…

Index: Kavanagh, Sarah A.; Piccinini, Alessandro; Connon, Stephen J. Advanced Synthesis and Catalysis, 2010 , vol. 352, # 11-12 p. 2089 - 2093

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Citation Number: 4

Abstract

Abstract 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.