Synthesis of Acyl Aminocyclopentenes with Acyl Anion Nucleophiles

Significance

The stereoselective ring-opening of diazabicycle 1 with acyl anions yielded only the anti diastereomer of 3. Under the mild reaction conditions, no isomerization of the alkene occurs in the final product. Previous Rh-catalyzed methods of carbonlyation of alkenes involved either high pressures of CO, and/or high temperatures. As a proof of concept, the procedure demonstrated that acyl anion equivalents can be generated under very mild and practical conditions. The methodology reported opens up the door to further study of the Rh-acylanion complex behavior.