A Robust and General Protocol for the Lewis??Base??Catalysed Reaction of Alcohols and Alkyl Propiolates

…, SJ Álvarez??Méndez, JM López??Soria…

Index: Tejedor, David; Alvarez-Mendez, Sergio J.; Lopez-Soria, Juan M.; Martin, Victor S.; Garcia-Tellado, Fernando European Journal of Organic Chemistry, 2014 , vol. 2014, # 1 p. 198 - 205

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Citation Number: 4

Abstract

Abstract A general and practical protocol for the tertiary-amine-catalysed synthesis of β- alkoxyacrylates from primary, secondary, and tertiary alcohols is described. Of the currently used catalysts, DABCO proved to be the best one for this process. Three factors seem to influence the outcome of the reaction:(1) the nucleophilic strength of the catalyst,(2) the electrophilicity of the intermediate ammonium acrylate, and (3) the pK a/nucleophilicity of ...