Catalytic cycloaddition of 2-hydroxy ketones with 1,1-dicyanoalkenes

Org Biomol Chem. 2016 Feb 7;14(5):1707-14. doi: 10.1039/c5ob02492g.

Abstract

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.