Synthesis of chiral ortho-substituted BIPHEP ligand and its application in asymmetric hydrogenation

ORGN 594

Xumu Zhang, Department of Chemistry, Pennsylvania State University, 152 Davey Lab, University Park, PA 16802, Shulin Wu, Department of Chemistry, Pennsylvania State University, 152 Davey Lab, University Park, PA 16802, and Minsheng He, Department of Chemistry, Penn State University, 152 Davey Lab, University Park, PA 16802.
Design and synthesis of chiral phosphine ligands are critical to development of highly enantioselective transition metal-catalyzed asymmetric reactions. Atropisomeric biaryl diphosphines are class of important ligands and have been shown broad utilities for catalytic asymmetric reaction. Herein we present an ortho-substituted BIPHEP ligand, o-Ph-MeOBIPHEP and its applications in Rh-catalyzed asymmetric hydrogenation. This ligand has been proved to be very effective in hydrogenation of alpha-(acylamino)- acrylic acids and other related substrates. High ees (97-99%) were obtained.

 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003