Diterpenoid Alkaloid Lappaconine Derivative Catalyzed Asymmetric α-Hydroxylation of β-Dicarbonyl Compounds with Hydrogen Peroxide

A new framework derived from the commercially available diterpenoid alkaloid lappaconitine was evaluated as a Bronsted base catalyst for the enantioselective alpha-hydroxylation of beta-dicarbonyl compounds by using 30% hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding alpha-hydroxy-beta-oxo esters, alpha-hydroxy-beta-oxo amides and (-)-kjellmanianone with up to 98% yield and 92% ee.