Building Addressable Libraries: Site-Selective Formation of an N-Acyliminium Ion Intermediate
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-α-methoxyalkyl amide to basic reaction conditions and the generality of the electrogenerated acid conditions for conducting microelectrode array reactions in a site-selective fashion.
David Kesselring, Karl Maurer and Kevin D. Moeller
Org. Lett., 2008, 10 (12), 2501–2504