title: Building addressable libraries: site-selective formation of an N-acyliminium ion intermediate.
abstract: A strategy for site-selectively generating reactive N-acyliminium ion intermediates on a microelectrode array has been developed. The route capitalizes on the use of an electroauxiliary for building a methoxylated amino acid substrate, and then the electrochemical generation and solution phase confinement of acid in order to form the N-acyliminium ion. Keys to this strategy were the stability of an N-alpha-methoxyalkyl amide to basic reaction conditions and the generality of the electrogenerated acid conditions for conducting microelectrode array reactions in a site-selective fashion.
authors.affiliation: Department of Chemistry, Washington University, St Louis, MO 63130, USA.
authors.forename: David
authors.initials: D
authors.lastname: Kesselring
authors.forename: Karl
authors.initials: K
authors.lastname: Maurer
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D008839:Microelectrodes; D015394:Molecular Structure
chemical_list: D007097:Imines