A Novel Catalyst System for the Efficient Syntheses of Chiral Alcohols

Categories: "Chemistry"

Reference #: 2006-003

OTC Contact: Sharon E. Pula, M.S., J.D. (Directory Information | Send a Message)

Description

Georgetown University is seeking a partner to commercialize a novel ligand catalyst system. Chiral alcohols represent a fundamental component of many active pharmaceuticals and intermediates. The chiral bisoxazolidine ligand developed at Georgetown is very effective in mediating the syntheses of a variety of chiral alcohols from aldehydes. Reactions performed with this system employ low cost alkyl zincs, making this catalyst an economical and cost-effective tool for synthesizing chiral alcohol products and intermediates.  The successful use of the chiral catalysts in asymmetric bond-forming reactions has been demonstrated.

Applications

This system is useful for the syntheses of chiral alcohol compounds from achiral aldehydes, and has many potential applications in the area of pharmaceutical products and intermediates. This system has been used in aldehyde alkylation, alkynylation and nitroaldol (Henry) reactions.

Advantages

  • The chiral ligand may be recycled.
  • Provides high yields (>87%) and enantioselectivities (>90%) for a wide range of substrates in various reactions
  • The catalyst system uses inexpensive alkyl-zinc reagents.

Stage of Development

The catalyst system has been synthesized and successfully applied in the catalytic enantioselective alkynylation of a range of aromatic and aliphatic aldehydes generating chiral alcohols in high yields and enantioselectivities.  The same system effectively catalyzed the asymmetric Henry reaction of aliphatic and aromatic aldehydes to produce β-hydroxy nitroalkanes in high yields and enantioselectivities.

Relevant Publications

“Bisoxazolidine-Catalyzed Enantioselective Alkynylation of Aldehydes.” J. Am. Chem. Soc., 2006, 128 (34), 10996-10997
“Chiral Amplification based on enantioselective dual-phase distribution of a scalemic bisoxazolidine catalyst.” Org. Lett., 2007, 9(16), 2965-8.
“Bisoxazolidine-catalyzed enantioselective alkynylation of aldehydes.” J. Am. Chem. Soc., 2006, 128(34), 10996-7.

Inventors

Christian Wolf and Shuanglong Liu

Patent Status

U.S. Patent Publication No. 7,763,734