4.5 Article

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

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 1, 页码 198-205

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301303

关键词

Alkynes; Organocatalysis; Amines; Alcohols; Vinyl ethers

资金

  1. Spanish Ministerio de Economia y Competitividad (MICINN)
  2. European Regional Development Fund [CTQ2011-28417-C01-01, CTQ2011-28417-C02-02]
  3. Spanish Ministerio de Educacion y Ciencia (MEC)

向作者/读者索取更多资源

A general and practical protocol for the tertiary-amine-catalysed synthesis of -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 the alcohol/alkoxide nucleophile. Reactivity tuning enables the transformation of a range of tertiary alcohols into the corresponding -alkoxyacrylate derivatives. Differences in the reactivity of different types of alcohol allow the selective transformation of diols containing two different hydroxy groups into the corresponding monoprotected derivatives. This protocol will aid other synthetic organic chemists to easily prepare such vinyl ethers under atom-economic, efficient, and bench-friendly reaction conditions.

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