Diarylketimine linker for solid phase organic synthesis: Applications to asymmetric diethyl zinc addtions

ORGN 779

Udaya Bhaskar Tadikonda, email.bhaskar@gmail.com1, Brian Douglas Dangel, briandangel@hotmail.com2, and Robin Polt, polt@u.arizona.edu1. (1) Department of Chemistry, University of Arizona, 1306 E University Blvd, Tucson, AZ 85721, (2) Department of Chemistry, Columbia University, 456 Riverside Dr. Apt 11C, New York, NY 10027
A 2-step synthesis and applications of robust diarylketimine linker on polystyrene support using commercially available Merrifield or 4-Bromo Wang resin has been described. Primary amines were loaded on to this linker either in the presence of TsOH or as hydrochloride salts in dichloromethane, acetonitrile or toluene as solvents. The use of this linker with tetradentate ligands as catalysts in asymmetric diethylzinc additions to aldehydes, and in the synthesis of small organic molecules, demonstrate the utility of this linker in organic reactions and its stability to wide range of reagents, and temperatures. On-bead characterization of ligands using C13-NMR, IR and UV spectroscopy to follow the reaction progress on the solid phase without cleavage is described.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005