A New Class of Ligands for Generating Enantiomerically Enriched Products

Technology #14761

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Researchers
Aaron Aponick
Flavio S. Pereira Cardoso
Managed By
Lenny Terry
Assistant Director 352-392-8929
Patent Protection
US Patent Pending US-2016-0222041-A1

Lowers the cost of manufacturing fine chemicals, flavors, and fragrances for the pharmaceutical and agricultural industries

This new class of heteroaromatic biaryl ligands will make enantioselective synthesis (the chemical process used to create molecules of defined three dimensional shape) less expensive and enable new reactions for the preparation of fine chemicals. Researchers at the University of Florida have developed a new class of biaryl ligands that will expand the current capabilities of state-of-the-art chemical synthesis by drastically altering the catalytic properties in a predictable and tunable manner. Of the biaryl ligands on the market today, QUINAP most closely matches the structure of this new class of ligands; however, it is prohibitively expensive and very difficult to modify compared to the newly developed class. The global market for catalysts is expected to reach $19.5 billion in 2016.

Application

Heteroaromatic biaryl ligands that will lower the cost and improve the efficiency of enantioselective synthesis to facilitate the production of chemicals, flavors, and fragrances

Advantages

  • Easily prepared and tuned, lowering costs
  • Outperforms existing biaryl ligands, increasing catalytic efficiency
  • Broadly applicable to a variety of different reaction classes and catalysis by different metals, maximizing versatility
  • Allows for the development of new compounds, providing opportunities for innovation in several industries

Technology

This new class of biaryl ligands capitalizes on an original concept for atropisomerism, whereby pi-stacking increases the barrier to rotation and enables the incorporation of 5-membered ring, electron-rich heterocycles in chiral biaryl ligands. These novel ligand structures have different steric and electronic properties than known ligands and are readily modified due to a highly convergent preparative route. This allows for easier ligand tuning, which lowers costs and increases efficiency in the enantioselective synthesis of non-racemic molecules for a variety of applications. The concept has been demonstrated using ligands prepared in high enantiomeric excess, showing that they impart high enantioselectivity in asymmetric reactions.