邻接
酰胺
烷基
化学
动力学分辨率
芳基
组合化学
多米诺骨牌
分子
催化作用
对映选择合成
立体化学
有机化学
作者
Yu‐Ping He,Rui Quan,Xing‐Zi Li,Jieping Zhu,Hua Wu
标识
DOI:10.1002/anie.202217954
摘要
An unprecedent asymmetric catalytic benzilic amide rearrangement for the synthesis of α,α-disubstituted piperazinones is reported. The reaction proceeds via a domino [4+1] imidazolidination/formal 1,2-nitrogen shift/1,2-aryl or alkyl migration sequence, employing readily available vicinal tricarbonyl compounds and 1,2-diamines as starting materials. This approach provides an efficient access to chiral C3-disubsituted piperazin-2-ones with high enantiocontrol, which are exceedingly difficult to access from the existing synthetic methodologies. The observed enantioselectivity was proposed to be controlled by dynamic kinetic resolution in the 1,2-aryl/alkyl migration step. The resulting densely functionalized products are versatile building blocks to bioactive natural products, drug molecules and their analogues.
科研通智能强力驱动
Strongly Powered by AbleSci AI