Horner-Wadsworth-Emmons Modification for Ramirez gem-Dibromoolefination of Aldehydes and Ketones Using P (Oi-Pr) 3

YQ Fang, O Lifchits, M Lautens

Index: Fang, Yuan-Qing; Lifchits, Olga; Lautens, Mark Synlett, 2008 , # 3 p. 413 - 417

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Citation Number: 24

Abstract

Abstract 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- ...