Dynamic imine libraries of [n�n] members can be self-sorted into just n pure products during the course of column chromatography on silica gel. Silica gel acts as an acid catalyst for imine metathesis, leading to rapid equilibration of all possible imines on the column. From that dynamic library, the least polar imine is eluted first. As its concentration is lowered, other imines that share either an aldehyde or an amine component with it will reequilibrate to produce more of it. As the polarity of solvent is increased, this process is iteratively repeated with more and more polar imines. We have demonstrated this adsorption-based self-sorting in practice of several [2�2] (example shown in Figure) and [3�3] imine libraries. Current work is focused on expanding this protocol to much larger dynamic imine libraries, as well as on the automation of this process through the use of high performance liquid chromatography (HPLC).                                                              

Adsorption-driven self-sorting of dynamic Imine libraries on silica gel

247th National Meeting (2014)

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