Département de Chimie Organique, Université de Genève, quai Ernest Ansermet 30, 1211, Geneva 4, Switzerland.
Laboratoire de Cristallographie, Université de Genève, quai Ernest Ansermet 24, 1211, Geneva 4, Switzerland.
Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13775-13779. doi: 10.1002/anie.201607574. Epub 2016 Oct 4.
N-aryl γ-lactams react intermolecularly with acceptor-acceptor diazo reagents, usually dicarbonyl compounds, in a copper-catalyzed process to yield functionalized pyrrolidines with α-pseudoquaternary centers. As 1,2-acyl or -phosphoryl migration is preferred, single regioisomers are obtained. Furthermore, in the presence of a Lewis acid, subsequent Friedel-Crafts reactions yield tricyclic pyrrolizidines in excellent yields (90-96 %) and diastereoselectivities (up to >20:1).
N-芳基γ-内酰胺与受体-受体重氮试剂（通常为二羰基化合物）在铜催化下进行分子间反应，生成具有α-伪季碳原子的功能化吡咯烷。由于 1,2-酰基或-膦酰基迁移是优先的，因此只得到单一的区域异构体。此外，在路易斯酸的存在下，随后的傅-克反应以优异的收率（90-96%）和非对映选择性（高达>20:1）得到三环吡咯里嗪。
