Tf 2 O-Promoted Intramolecular Schmidt Reaction of the ω-Azido Carboxylic Acids

作者：Xuejuan Wang, Yan Su, Rui Li, Peiming Gu · 发表于：The Journal of Organic Chemistry · 年份：2018 · DOI：10.1021/acs.joc.8b00475 · 被引用次数：17 · 研究领域：Chemical Synthesis and Analysis、Synthesis and Catalytic Reactions、Click Chemistry and Applications

A designed Tf 2 O-promoted intramolecular Schmidt reaction of 2-substituted ω-azido carboxylic acids was demonstrated. Tf 2 O was used as an activation reagent for the carboxylic acid, and ω-azido anhydride was in situ generated, releasing a molecular TfOH, which acted as an acid promoter for the Schmidt process. A series of 2-substituted pyrrolidines was produced and acetylated for better purification. The strategy was also efficient for conversion of a 4-substituted ω-azido carboxylic acid to the tricyclic lactam.