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.

以金鸡纳生物碱催化剂（cinchona alkaloid catalyst）催化，将脯氨酸衍生的三酮哌嗪（TKP）与β-取代烯酮、丙烯酰胺进行迈克尔加成反应（Michael addition），可高产率、高对映体比例（er）得到带有双环[2.2.2]二氮杂辛烷结构（bicyclo[2.2.2]diazaoctane structure）的产物。此外，本研究还展示了对该酰胺类产物进行进一步修饰，以构建与异戊烯基化生物碱家族成员结构相似的多环骨架。