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Tf2O‑Promoted Intramolecular Schmidt Reaction of the ω‑Azido Carboxylic Acids

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journal contribution
posted on 18.04.2018, 00:00 by Xue-Juan Wang, Yan Su, Rui Li, Peiming Gu
A designed Tf2O-promoted intramolecular Schmidt reaction of 2-substituted ω-azido carboxylic acids was demonstrated. Tf2O 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.