Applications of chiral biphenol-based bidentate diphosphonite and monophosphoramidite ligands to Pd-catalyzed intramolecular asymmetric allylic amination reactions

ORGN 660

Chi-Feng Lin, corey84064@gmail.com1, Chih-Wei Chien, chchien@ic.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) Institute of Chemical Biology and Drug Discovery, State University of New York, Stony Brook, NY 11794-3400
Among the methods of asymmetric synthesis, transition-metal catalyzed asymmetric transformations have proven to be a highly efficient and practical approach to induce desired chirality. In our lab, libraries of biphenol-based bidentate diphosphonite and monophosphoramidite ligands have been developed which are very effective in various catalytic asymmetric reactions. Herein we present the application of a Pd-catalyzed intramolecular asymmetric allylic amination reaction to the preparation of enantiopure key intermediates in the total syntheses of Schulzeines A-C and (-)-O-methylthaicanine.