Copper-Catalyzed [2 + 3] Cyclization of α-Hydroxyl Ketones and Arylacetonitriles: Access to Multisubstituted Butenolides and Oxazoles.

A copper-catalyzed [2 + 3] formal cyclization reaction between alpha-hydroxyl ketones and arylacetonitriles has been developed. The reaction outcome was ultimately dependent on the structure of the alpha-hydroxy ketones employed. Tertiary alpha-hydroxy ketones gave 3,4,5,5-tetrasubstituted butenolides as the sole products, while secondary alpha-hydroxy ketones furnished 2,4,5-trisubstituted oxazoles selectively. This method has many advantages, such as the use of easily available substrates, broad substrate scope, good functional tolerance, and milder reaction conditions.