A Practical Method for the Synthesis of 2-Alkynylpropenals

摘要

A general method for the preparation of 2-alkynyl acroleins is described beginning with vinyl iodide 5 and involving a combination of Sonogashira coupling and Dess-Martin oxidation.Critical to the success of this approach is the use of a special workup procedure for the oxidation step.The resultant enynals participate in a variety of addition reactions including aldol condensations and reactions with organolithium compounds.