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

Shi-Heng HungYu-Min WangYi-Hung LiuSHIUH-TZUNG LIU2024-09-182024-09-182024-08-23https://scholars.lib.ntu.edu.tw/handle/123456789/720995A 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.enPreparation of 4-Allenyloxazolines from (<i>Z</i>)-2-En-4-yn-1-ol via Propargyl/Allenyl Isomerizationjournal article10.1021/acs.joc.4c01152