Siloxyalkyne-Alkene Metathesis: Rapid Access to Highly Functionalized Enones

Area of Science:

• Organic Chemistry
• Catalysis
• Synthetic Methodology

Background:

• Intramolecular reactions are crucial for constructing complex molecular architectures.
• Ruthenium (Ru)-catalyzed metathesis offers powerful tools for carbon-carbon bond formation.
• Developing efficient synthetic routes to functionalized enones is a persistent challenge in organic chemistry.

Purpose of the Study:

• To develop a novel synthetic method for highly functionalized enones.
• To explore the utility of siloxyalkynes in ruthenium-catalyzed intramolecular reactions.
• To demonstrate the broad applicability of the developed method for synthesizing diverse cyclic compounds.

Main Methods:

• Intramolecular ruthenium-catalyzed metathesis of siloxyalkynes with terminal alkenes.
• Protodesilylation for the removal of the silyl group.
• Synthesis of heterocyclic and polycyclic compounds from acyclic precursors.

Main Results:

• A new synthetic method for highly functionalized enones was successfully developed.
• The reaction proceeds via mechanistically intriguing participation of siloxyalkynes.
• Efficient synthesis of various heterocyclic and polycyclic compounds was achieved, demonstrating the method's generality.

Conclusions:

• The developed method provides an efficient and versatile route to highly functionalized enones.
• This approach expands the synthetic utility of siloxyalkynes in ruthenium-catalyzed transformations.
• The methodology is applicable to the synthesis of complex heterocyclic and polycyclic structures.