Horner-Wadsworth-Emmons Modification for Ramirez gem-Dibromoolefination of Aldehydes and Ketones Using P(Oi-Pr)3
2008
A simple procedure for the use of triisopropylphosphite in the Ramirez olefination is described. This reagent is equally or more reactive than PPh 3 toward aldehydes and ketones in the GEM-dibromoolefination of aldehydes and ketones. Under the reaction conditions, an α-bromoketone gave a novel tribromomethyl-substituted oxirane product in good yield. The substrate-dependent nature of this reaction suggests that this Horner-Wadsworth-Emmons equivalent of the Ramirez GEM-dibromoolefination reaction proceeds through an ionic mechanism.
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