Access to spirocyclic vinyl sulfones via radical cyclization and functional group migration

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Spirocyclic vinyl sulfones combine 3D spiro structures with Michael acceptor reactivity.
• These compounds show potential for novel biological activities.
• Efficient synthesis methods are lacking, hindering drug discovery applications.

Purpose of the Study:

• To develop a practical and versatile synthetic approach for multi-functionalized spirocyclic vinyl sulfones.
• To enable broader investigation of these compounds in drug discovery.

Main Methods:

• A cascade reaction involving radical cyclization followed by (hetero)aryl migration.
• Utilized mild photocatalytic conditions.
• Employed easily available starting materials.

Main Results:

• Achieved efficient synthesis of diverse spirocyclic vinyl sulfones.
• Demonstrated a versatile protocol for constructing complex molecular scaffolds.
• Successfully synthesized medium-sized ring-fused spirocyclic vinyl sulfones.

Conclusions:

• The developed method provides efficient access to valuable spirocyclic vinyl sulfone scaffolds.
• This work facilitates further exploration of spirocyclic vinyl sulfones in medicinal chemistry and drug discovery.