Diterpenoid alkaloid lappaconine derivative catalyzed asymmetric α-hydroxylation of β-dicarbonyl compounds with hydrogen peroxide

Abstract

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. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.