Palladium-Catalyzed Decarboxylative (3 + 3) Coupling Cyclization toward Diverse Fully Substituted Unsaturated...

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Glutarimide derivatives are important scaffolds in medicinal chemistry.
• Efficient synthetic routes to highly substituted glutarimides are desirable.
• Palladium-catalyzed reactions offer powerful tools for C-C bond formation.

Purpose of the Study:

• To develop a novel palladium-catalyzed decarboxylative coupling cyclization reaction.
• To synthesize fully substituted unsaturated glutarimide derivatives.
• To demonstrate the practical utility and scope of the developed method.

Main Methods:

• Palladium-catalyzed decarboxylative (3 + 3) coupling cyclization reaction.
• Utilized vinyloxazolidine-2,4-diones and cyclopropenones as starting materials.
• Performed scale-up experiments, asymmetric transformations, and product derivatizations.

Main Results:

• Successfully synthesized a variety of fully substituted unsaturated glutarimide derivatives.
• Demonstrated the practical utility of the method through scale-up and asymmetric synthesis.
• Preliminary mechanistic studies indicated Pd(0) cleavage of the cyclopropenone C-C bond as the initial step.

Conclusions:

• A novel and efficient palladium-catalyzed decarboxylative (3 + 3) coupling cyclization reaction has been established.
• The developed method provides access to diverse, highly substituted glutarimide derivatives.
• The reaction exhibits practical utility and potential for further development in asymmetric synthesis.