Module 10 : Organocatalysis

Lecture 35: Alkaloid Based Reactions

The 6'-OH cinchona alkaloid L-9 is an excellent catalyst for the reaction of α- ketoesters with nitromethane (Scheme 12). The highly enantioenriched products from the Henry reaction could be elaborated to aziridines, β- lactams and α -alkylcysteines. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of α-ketoesters .

Scheme 12. Cinchona-Catalyzed in Henry Reaction

Bifunctional cinchona alkaloid-thiourea L10 can catalyze efficiently the aza-Henry reaction of cyclic trifluoromethyl ketimines with nitromethanes (Scheme 13). The title reaction can provide biologically interesting chiral trifluoromethyl dihydroquinazolinone frameworks with high yield and enantioselectivity.

Scheme 13. Cinchona-Catalyzed in Henry Reaction