Study of a new ‘chiral proton’ organocatalyst with hydrolase activity: application in azlactone racemic dynamic resolution

Abstract For the first time, a 1,3-ketoenol system is described as an acid catalyst with hydrolytic activity. The combination of an enol and a pyridine/benzimidazole supported on a benzofuran skeleton allowed the creation of a novel bifunctional organocatalyst, which has been applied in azlactone racemic dynamic resolution. In spite of the moderate enantioselectivities obtained, the catalyst constitutes a novel concept in the field of chiral Bronsted acid catalysis.