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An Unusual Chemoselective Cycloaddition of Nonstabilized Azomethine Ylide: Synthesis of Oxazolidine Derivatives

Year: 2025

Type: article

Abstract: An unusual [3 + 2] cycloaddition involving nonstabilized azomethine ylides and unsaturated carbonyl compounds is reported, wherein the reaction exclusively occurs at the carbonyl group rather than the conjugated double bond. This annulation strategy enables the efficient synthesis of a diverse range of substituted oxazolidine frameworks with excellent yields (up to 96%) under mild reaction conditions. Control experiments suggest that the unexpected selectivity likely arises from the electron-withdrawing ester group adjacent to the carbonyl, which enhances its reactivity.

Source: Chemistry - An Asian Journal

DOI: 10.1002/asia.70392