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Building addressable libraries: site-selective formation of an N-acyliminium ion intermediate
David Kesselring1, Karl Maurer, Kevin D Moeller
1Department of Chemistry, Washington University, St Louis, MO 63130, USA.
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.
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