Synthesis of chiral binaphthyl phospholane and phosphepine ligands and their applications in highly enantioselective hydrogenation of beta-amino acid derivatives

ORGN 83

Xumu Zhang, Wenjun Tang, and Weimin Wang. Department of Chemistry, Pennsylvania State University, 152 Davey Lab, University Park, PA 16802
The synthesis of chiral beta-amino acids has drawn a great deal of attention due to its importance in biomedical research and the pharmaceutical industry. Compared with several stoichiometric and catalytic methods reported, direct hydrogenation of 3-aminoacrylic acid derivatives represents one of the simplest and most efficient routes. In this presentation, we report the syntheses and applications of chiral bisphospholane (Tangphos) and bisphosphepine (Binapine) ligands. High enantioselectives (>99% ee) and turnover numbers have been obtained in Rh-catalyzed hydrogenation of beta-amino acid derivatives.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004