Office of Technology Transfer – University of Michigan

Chiral Spiroketal-Based C2-Symmetric Scaffold for Asymmetric Catalysis

Technology #7406

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Researchers
Pavel Nagorny
Managed By
Jeremy Nelson
Patent Protection
US Patent Pending

Chemical incorporation of a chiral center is important in a number of industrial applications including pharmaceuticals and material sciences. Incorporation of chiral centers often relies upon the utilization of chiral ligands that enable the absolute configuration of chiral center to be set. A number of privileged scaffolds, including chiral C2-symmetric ligands (BINOL and SPINOL), are frequently used for these transformations. However, the drawbacks of these privileged scaffold ligands often include difficult synthesis, cost ($150 - $400/g), and the need for subsequent enantiomeric resolution.

Chiral Spiroketal-Based C2-Symmetric Scaffolds (OSPINOL) for Asymmetric Catalysis

C2-symmetric spiroketal based scaffolds can be synthesized without resolution in 3-5 steps in large-scale quantities. These chiral ligands have shown utilization in asymmetric catalysis applications including hydrogenation and acylation reactions.

Applications

  • Asymmetric catalysis applications
  • Medicinal Chemistry
  • Material Science

Advantages

  • Easy to synthesize (3-5 steps)
  • Requires no chiral purification
  • Enhanced properties versus that of SPINOL (improved ee% and different chemical-physical properties)