Synthesis of Optically Active Indoline Derivatives via Ruthenium (II)-Catalyzed Enantioselective C-H Functionalization

Overview of Technology

Provides a cost-effective, easy preparation, versatile and distinct reactivity for customization of the 4-formyl indoline derivatives

Background 

This novel technology allows for some customization of the RU(II)-catalyzed method during asymmetric synthesis. Using the 4-formylindoline derivative (compound based on the indole structure with a 2-3 bond that is saturated), research has proven that Ru(II) arene complexes are a favorable catalyst for C-H activation/hydroacylation owing to their cost-effectiveness, easy preparation, versatile and distinct reactivity and selectivity. The result of testing and research of concluded in 4-formylindoline transformation, enabling access to optically tricyclic compound that is of potential biological and pharmaceutical interest.

Description of Technology

This novel technology allows for some customization of the RU(II)-catalyzed method during asymmetric synthesis. Using the 4-formylindoline derivative (compound based on the indole structure with a 2-3 bond that is saturated), research has proven that Ru(II) arene complexes are a favorable catalyst for C-H activation/hydroacylation owing to their cost-effectiveness, easy preparation, versatile and distinct reactivity and selectivity. The result of testing and research of concluded in 4-formylindoline transformation, enabling access to optically tricyclic compound that is of potential biological and pharmaceutical interest.

Benefits

Compared to previous rhodium and palladium‑catalyzed systems, which would be able to make the same product but have never been demonstrated, this system uses ruthenium as a relatively much cheaper metal source as the catalyst. The chiral co‑catalyst is readily available from various companies.

  • Practical
  • Cost-Effective

Applications

  • Pharmaceutical development
  • Biological development and studies

Opportunity

Mississippi State University are looking to work with pharmaceutical companies and companies that develop organic intermediates, who are likely to use this method for the production of indoline and the related tricyclic compounds.

IP Status

  • Patent pending

 

Patent Information: