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Preparation of 4‑Allenyloxazolines from (Z)‑2-En-4-yn-1-ol via Propargyl/Allenyl Isomerization

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posted on 2024-08-23, 13:06 authored by Shi-Heng Hung, Yu-Min Wang, Yi-Hung Liu, Shiuh-Tzung Liu
A novel method for the preparation of 4-allenyl-oxazolines 2 is described via the reaction of 2-en-4-yn-1-ols 1 with trichloroacetonitrile in the presence of DBU. Reaction proceeds through the nucleophilic attack of OH functionality in 1 to CCl3CN followed by cyclization, propargyl/allene isomerization, and protonation. In this investigation, it is noticed that propargyl/allene isomerization is sensitive to the substituents.

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