Columbia University

Technology Ventures

Synthesis of asymmetric carbinamines with silacycle compounds

Technology #m04-064

Asymmetric molecules with non-superimposable mirror images serve as important building blocks in synthetic organic chemistry and can be produced using silacycle compounds. This technology identifies silacycle compounds that facilitate synthesis of asymmetric carbinamines which are useful organic compounds. By favoring the addition reaction in a particular orientation, silacycle compounds enhance the synthetic yield of asymmetric carbinamines.

Silacycle compounds a less expensive asymmetric synthesis processes than existing methods

The silacycle reagents identified in this technology may reduce the need for expensive separations that are commonly used to prepare asymmetric molecules. In addition, the silacycle compounds are generated using reagents that are inexpensive and can be recovered for future use.

The synthesis of asymmetric carbinamines with silacycle compounds has been demonstrated with benzoylhydrazone and a range of aromatic compounds.

Lead Inventor:

James L. Leighton, Ph.D.


  • Preparation of silacycle compounds.
  • Synthesis of asymmetric carbinamine compounds.


  • Low cost synthesis of asymmetric carbinamines.
  • Uses less toxic silacycle compounds than existing reagents.
  • Can be used for large scale synthesis.
  • Can react with a wide range of imine reagents.

Patent information:

Patent Pending (US 2008167468)

Tech Ventures Reference: IR M04-064

Related Publications:

Patent No. 8,642,798