The Journal of Organic Chemistry

A facile synthesis of 3, 4-dienamides by the reaction of propargyl alcohols with cyclic amide acetals, and their stereoselective rearrangement to 2 (E), 4 (Z)-dienamides …

S Tsuboi, Y Nooda, A Takeda

Index: Tsuboi, Sadao; Nooda, Yuji; Takeda, Akira Journal of Organic Chemistry, 1984 , vol. 49, # 7 p. 1204 - 1208

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Citation Number: 22

Abstract

Thermal condensation of propargyl alcohols with acetals of 1-acetylpyrrolidine and 1- acetylpiperidine gave 3, Cdienamides in good yields. Alumina promoted the rearrangement of j3-allenic amides to 2@), 4 (Z)-dienamides stereoselectively. Ita application to the synthesis of isochavicine of pepper components is described. Carbon-13 NMR data of these dienamides were obtained.