A Tunable Route for the Synthesis of Azomethine Imines and β‑Aminocarbonyl Compounds from Alkenes

Cyclic azomethine imines possessing a β-aminocarbonyl motif are accessed from simple alkene and hydrazone starting materials. A thermal, concerted alkene aminocarbonylation pathway involving an imino-isocyanate intermediate is proposed and supported by DFT calculations. A notable feature of the process is the steric shielding present in the dipoles formed, which allows for facile purification of the products by chromatography or crystallization. In addition, a fluorenone-derived reagent is reported, which provides reactivity with several alkene classes and allows for mild derivatization of the dipoles into β-aminoamides, β-aminoesters, and β-amino acids.