Development of chiral biphenol-based phosphorus ligands and their applications to asymmetric allylic amination reactions

ORGN 560

Ce Shi, cshi@ic.sunysb.edu1, Stephen Chaterpaul1, and Iwao Ojima, iojima@notes.cc.sunysb.edu2. (1) Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400, (2) Department of Chemistry and ICB&DD, State University of New York at Stony Brook, The Chemistry Bldg, Stony Brook, NY 11794-3400
New classes of phosphorus ligands based on axially chiral biphenols have been designed and developed in our laboratory. The salient feature of those newly developed ligands is their fine-tuning capability through systematic modifications at the 3,3'-positions of biphenol moieties as well as the substituents on the phosphorus atom. Those modifications have proved to play an important role on achieving high enantioselectivity and reactivity in various asymmetric reactions. To demonstrate the efficacy of our ligands in asymmetric allylic substitution reactions, two Pd-catalyzed asymmetric allylic amination reactions have been investigated. We will present our newly designed library of phosphorus ligands and the structure-efficacy relationship study on these reactions.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007