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 Brønsted base catalyst for the enantioselective α‐hydroxylation of β‐dicarbonyl compounds by using 30 % hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding α‐hydroxy‐β‐oxo esters, α‐hydroxy‐β‐oxo amides and (–)‐kjellmanianone with up to 98 % yield and 92 % ee. Ten new organocatalysts derived from the diterpenoid alkaloid lappaconitine are described. Activities for the enantioselective α‐hydroxylation of β‐dicarbonyl compounds with 30 % hydrogen peroxide as a green and practical source of oxygen is described. This protocol allows convenient access to the corresponding α‐hydroxy‐β‐dicarbonyl compounds with up to 98 % yield and 92 % ee under mild conditions.