Metal-mediated reactions of aryl isocyanates with dimethoxycarbene to form isatin derivatives

Hydantoin derivatives have been established as the observed product in the reaction of aryl isocyanates with dimethoxycarbene. A change in the reactivity profile of dimethoxycarbene with aryl isocyanates was observed upon the addition of a metal species. Methodology has been developed in which the outcome of nucleophilic carbene reactions with isocyanates can be controlled with simple changes to reaction conditions.