Development of chiral biphenol-based monodentate phosphoramidite ligands and their application to the intramolecular asymmetric allylic amination reaction

ORGN 131

Ce Shi, cshi@ic.sunysb.edu, Bruno D. Chapsal, bchapsal@ic.sunysb.edu, Kimberly Odynocki, and Iwao Ojima, iojima@notes.cc.sunysb.edu. Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400
A new class of monodentate phosphoramidite ligands based on axially chiral biphenols have been designed and developed in our laboratory. These ligands possess fine-tuning capability through systematic modifications not only on the amine moiety but also on the 3,3'-positions of biphenol moiety. 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, we have selected a Pd-catalyzed intramolecular asymmetric allylic amination reaction, which leads to the formation of chiral 1-substituted tetrahydroisoquinoline skeleton. We will present our newly designed library of phosphoramidite ligands and the structure-efficacy relationship study on this reaction.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006