Boronic Acid-Catalyzed, Highly Enantioselective Aza-Michael Additions of Hydroxamic Acid to Quinone Imine Ketals

Abstract

Boronic acid is one of the most versatile organic molecules in chemistry. Its uses include organic reactions, molecular recognition, assembly, and even medicine. While boronic acid catalysis, which utilizes an inherent catalytic property, has become an important research objective, it still lags far behind other boronic acid chemistries. Here, we report our discovery of a new boronic acid catalysis that enables the aza-Michael addition of hydroxamic acid to quinone imine ketals. By using 3-borono-BINOL as a chiral boronic acid catalyst, this reaction could be implemented in a highly enantioselective manner, paving the way to densely functionalized cyclohexanes.