ORGN 84 |
Asymmetric hydrogenation of functional olefins and ketones with TunePhos–Ru catalysts
| Xumu Zhang, Shulin Wu, Wenjun Tang, Aiwen Lei, and Minsheng He. Department of Chemistry, Pennsylvania State University, 152 Davey Lab, University Park, PA 16802 |
| Asymmetric hydrogenation of C=C, C=O and C=N double bonds provides a versatile method to prepare enantiopure chiral compounds. Design and synthesis of chiral biaryl diphosphine ligands are critical to development of highly efficient Ru-catalyzed asymmetric hydrogenation. One recent highlighted topic in this area is concerned with the dihedral angles of chiral backbone of phosphine ligand which can exert important effects on enantioselectivity of asymmetric reactions. We have recently developed a class of biphenyl diphosphine ligands with tunable dihedral angles of chiral backbones (Cn-TunePhos) and demonstrated their utilities in several reactions. Here we report their applications in Ru-catalyzed asymmetric hydrogenations. These reactions can be used to prepare valuable chiral hydroxy esters, cyclic amino acids and amino alcohols with high ee values. A practical synthesis of C3-TunePhos will also be presented. 
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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
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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