Regioselective synthesis of benzyl aryl amine disassembling dendrons

CHED 854

Dominic V. McGrath, Charles S. Shanahan, and Adrian Ortiz. Department of Chemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721
We have previously used oligomeric systems to model dendrimers that have the ability to disassemble under strictly controlled conditions. The favorable results of the disassembly kinetics of these compounds prompted the incorporation of a similar disassembly pathway into full dendritic systems. Initially the synthesis of these dendrons proved to be inefficient, relying on the selective alkylation of a 3,4-dihydroxy benzoic acid derivative. To overcome these synthetic limitations, a 3-hydroxy-4-amino benzoic acid derivative was used to allow for complete regioselectivity of the alkylation steps. The synthesis of these dendrons proceeded not only with higher selectivity, but allowed for the investigation of a new benzyl amine disassembly pathway.