Catalytic Cycloaddition of 2-Hydroxy Ketones with 1,1-Dicyanoalkenes.

A tin-catalyzed reaction of α-hydroxy ketones with 1,1-dicyanoalkenes produced 2-amino-4,5-dihydrofuran-3-nitriles. In the catalytic reaction, tin enolates were generated from α-hydroxy ketones as active catalytic species. The highly basic ability of the Sn-O bonds played an important role in the reactions. This tin-catalyzed reaction was highly atom-economical and required no other metal reagents.