Use of N-allylidene-1,1-diphenylethanamine as a latent acrolein synthon in the double nucleophilic addition reaction of ketene silyl (Thio)acetals and allylborolanes.

In the presence of silica gel and water, a mixture of ketene silyl acetals and 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane underwent 1,4- and subsequently 1,2-addition with N-allylidene-1,1-diphenylethanamine to give delta-hydroxyesters in good yields, where the allylideneamine was successfully used as an acrolein equivalent.