Reactivity switching on solid support: solid-phase synthesis of tertiary amines by reduction of tertiary amides with LiAlH4

Reactivity of LiAlH4 was controlled by using solid-phase reaction conditions. Tertiary amides bound to gel-type polystyrene support were reduced with LiAlH4 to give tertiary amines with satisfactory purity, whereas the reduction of similar tertiary amides in solution gave secondary amines as main products. Solid-phase synthesis of tertiary amine libraries was achieved by using this method.