Development of biphenol-based fine-tunable phosphoramidite ligands and their applications to the catalytic asymmetric allylic substitution reactions

ORGN 654

Ce Shi, cshi@ic.sunysb.edu1, Bruno D. Chapsal, bchapsal@ic.sunysb.edu1, Hojae Choi, hojchoi@ms.cc.sunysb.edu1, 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
Transition metal-catalyzed asymmetric allylic substitution is a powerful tool for the formation of carbon-carbon and carbon-heteroatom bonds. Bidentate phophorus ligands have been used extensively to control regioselectivity and enantioselectivity. We have been developing a new class of chiral monodentate phosphoramidite ligands based on enantiopure biphenols. These ligands are easy to prepare and fine-tunable through modification of the R1, R2 and R3 groups. We will present our newly designed library of phosphoramidite ligands and their use in the study of a variety of catalytic asymmetric reactions, including allylic alkylation, allylic etherification and allylic amination.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005