Reactions of propargyl alcohols with amide acetals

…, JJ Petraitis, RW Kosley Jr, SL Buchwald

Index: Parker, Kathlyn A.; Petraitis, Joseph J.; Kosley, Raymond W.; Buchwald, Stephen L. Journal of Organic Chemistry, 1982 , vol. 47, # 3 p. 389 - 398

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Citation Number: 23

Abstract

Background The reaction of an allylic alcohol with a acetamide dialkyl acetal3 or a substituted acetamide dialkyl acetal4 has proved a popular alternative to the classical Claisen rearrangement as a method of obtaining y, b-unsaturated carbonyl compounds. While 3-methyl-4-penten-1-yn-3-01 (1) 5 undergoes the predicted ortho ester Claisen rearrangement, 6 treatment of this alcohol with dimethylacet-