General combinatorial synthesis of tertiary amines on solid support. A novel conditional release strategy based on traceless linking at nitrogen

A novel solid phase synthesis of tertiary amines involving iodide-induced cleavage of the NO bond of resin bound alkoxyammonium intermediates is described. The quaternary intermediates were assembled via sequential reductive aminations followed by alkylation. Cleavage from the solid support was induced by iodide ion or base, to afford the target tertiary amines in excellent purity.