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Synthesis of Diverse N-Acryloyl Azetidines and Evaluation of Their Enhanced Thiol Reactivities.

Acyl azetidines exhibit nonplanar hybridization, leading to lower amide-like character of the corresponding (O)C-N bonds. This impacts N-acryloyl azetidines by producing enhanced electrophilicy at appended Michael acceptors. Herein, reactivity data are reported in the presence of glutathione (GSH) in phosphate buffer (pH 7.4) at 37 °C. Wide reactivity ranges are observed by varying substitution at the Michael acceptor or by modulating the electron-withdrawing character of substituents at the C3 position of the azetidine.