Columbia Technology Ventures

An inexpensive organocatalyst for scalable and highly enantioselective chemical transformations

Chiral centers are ubiquitous in many commercially produced chemicals, such as pharmaceuticals. Generation of these chiral centers often involves the use of expensive and difficult-to-use transition metals, increasing the cost and difficulty of production. This technology is a cyclopropene imine able to catalyze a number of different transformations enantioselectively. These cyclopropene imines are analogous to guanidines, yet are much more basic. The added basicity makes cyclopropene imines a much more general solution to Bronsted base catalysis, and operationally simpler and less expensive than most transition-metal based catalysis. This technology may result in the development of an inexpensive organic catalyst for the production of enantiopure pharmaceuticals, fragrances, flavors, and research chemicals on both laboratory and process scales.

Tunable and easily synthesized catalyst allows for higher-yielding reactions, increasing production output

The extraordinary versatility of this technology can be attributed, in part, to its easily modified structure, allowing the catalyst to be optimized for many distinct reaction conditions. The preparation of the catalysts can be done on a multi-gram scale and is significantly cheaper to synthesize than comparable catalysts. As such, simple optimization of this catalyst can allow it to integrate fluidly with existing proprietary processes. This technology may allow the synthesis of valuable chemical compounds in high yield with high enantiomeric excess faster and more easily than conventional processes.

This technology has been validated as a competent catalyst for multiple conjugate addition reactions, with high enantiomeric excess being validated by chiral HPLC.

Lead Inventor:

Tristan Lambert, Ph.D.

Applications:

  • Asymmetric Michael reactions
  • Asymmetric base catalyzed conjugate additions
  • Base catalyzed reactions
  • Synthesis of natural and unnatural amino acids in enantiopure form
  • Synthesis of 1,5 amino acids

Advantages:

  • Very low cost catalyst
  • All organic, does not use any metals
  • Catalyst is easily synthesized on large scale
  • Catalyst is easily optimized
  • Fast reaction times
  • Effective for a range of transformations

Patent Information:

Patent Pending (US 20140288323)

Tech Ventures Reference: IR CU12115

Related Publications: