AI Article Synopsis

  • A new method has been created for selectively generating reactive N-acyliminium ion intermediates using a microelectrode array.
  • This method involves using an electroauxiliary to create a specific methoxylated amino acid before generating acid electrochemically, which helps in forming the N-acyliminium ion.
  • Key factors include the stability of the N-alpha-methoxyalkyl amide under basic conditions and the ability to conduct selective reactions on the microelectrode array using the electrogenerated acid.

Article 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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http://dx.doi.org/10.1021/ol8007827DOI Listing

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