An Asymmetric Organocatalysis Approach to the Prenylated Alkaloid Family

Michael addition
of a proline-derived triketopiperazine (TKP) to
β-substituted enones and acrylamides, mediated by a cinchona
alkaloid catalyst, delivers products possessing a bicyclo­[2.2.2]­diazaoctane
structure in high yield and enantiomeric ratio (er). Further modification
of the amide products toward polycyclic scaffolds resembling members
of the prenylated alkaloid family is also demonstrated.