A family of compounds that can be used as catalysts in asymmetric synthesis.

The Need

Traditional transition metal catalysts are the current state of art in chemical catalysis and, while highly functional, they can significantly reduce the amount of usable product, leaving impurities in the compound which are difficult to separate out. These catalysts can be expensive, with prices ranging from $19.20 – $183.91/mmol, and require a highly controlled environment with minimal to no oxygen/moisture exposure. Relatively few asymmetric catalytic processes have been reported which employ organic molecules as catalysts despite their vast potential and widespread availability in optically pure forms.

The Market

  • The removal of post-reaction transition metal residues from pharmaceutical products often leads to problems such as high costs, time loss, low efficiency, and reduced yields.
  • Requirements for low parts-per-million levels of trace metals and enantiomeric yields of above 99% further justifies the need for alternatives to transition metal catalysts, preferably organocatalysts that can drive asymmetric synthesis.
  • The growing size of the market for enantiomerically pure compounds is driven primarily by increasingly stringent government regulations in the pharmaceutical industry as well as companies introducing enantiomerically pure versions of previously patented racemic compounds to retain property rights.
  • This chemical innovation addresses the ongoing industry-wide need of reducing costs without foregoing efficient production of enantiopure compounds by inherently being cheaper than its metal-based counterparts as well as eliminating the need for post-production separation of metal residue.
  • The timeliness of this new discovery is evidenced by the recent shift towards “green chemistry”, in which the production of chemicals is becoming more focused on reducing toxic reagents and by-products.

The Technology

The Ohio State University researchers, led by Dr. Mattson, developed an invention that is a family of enantiopure silanediol compounds used as catalysts in asymmetric synthesis. Dr. Mattson produces these compounds at a lower cost compared to the current gold standard, with an estimated cost per mmol of around $5.20. The catalysts are metal-free with low toxicity and made from renewable resources, properties that are crucial when considering the importance of separating transition metal residue from biologically relevant targets in the context of pharmaceuticals. The compounds have excellent shelf-stability even in ambient conditions and it is not necessary for the compounds to be kept oxygen/moisture-free during the reactions, unlike traditional transition metal catalysts. They are readily prepared from commercially available starting materials, and are capable of catalyzing a variety of organic reactions with a diverse range of different substrates. Currently, the American Chemical Society Petroleum Research Fund, the Ohio State Department of Chemistry and Biochemistry and the National Science Foundation fund the research.

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