Columbia University

Technology Ventures

Silacycle reagents for asymmetric allyl addition

Technology #m02-042

Asymmetric molecules with non-superimposable mirror images serve as important building blocks in synthetic organic chemistry and can be produced using silacycle reagents. This technology describes allylic silacycle reagents that can selectively add carbon substituents called allyls to one side of an aldehyde molecule to produce asymmetric allylic alcohols. These reagents are also capable of asymmetric allyl addition to other organic compounds such as aldols and hydrazines.

Silacycle reagents are more stable, less toxic, and less expensive than comparable existing.

Compared to other reagents for asymmetric allyl addition, silacycle reagents are less expensive to prepare, more stable and less toxic. Therefore, silacycle reagents can be prepared and stored in advance of performing reactions. Silacycle starting reagents are also easily separated from their allylic products. Finally, silacycle reagents can be broadly used for asymmetric allyl additions to different functional groups.

The high yield and selectivity of silacycle reagents has been demonstrated with a range of different organic compound starting materials.

Lead Inventor:

James L. Leighton, Ph.D.

Applications:

  • Preparation of asymmetric allylic silanes for chemical synthesis.
  • Asymmetric addition of allyls to aldehydes and hydrazines.
  • Diastereoselective aldol allylation to produce diols.

Advantages:

  • Silacycle reagents are stable and have low toxicity.
  • Less expensive preparation compared to existing reagents.
  • Separable reaction products.

Patent information:

Patent Issued (US 7,534,905)

Tech Ventures Reference: IR M02-042

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