A Cu-catalyzed four-component cascade reaction to construct beta-ester-gamma-amino ketones

作者：Ling, Jiayue; Zhang, Jie; Zhao, Yanwei; Xu, Yudong; Wang, Hanghang; Lv, Yuanzheng; Ji, Meishan; Ma, Liang; Ma, Meihua; Wan, Xiaobing^*

来源：Organic and Biomolecular Chemistry, 2016, 14(23): 5310-5316.

DOI：10.1039/c6ob00873a

• H INSERTION REACTIONS
• HIGHLY ENANTIOSELECTIVE INSERTION
• KORNBLUM-DELAMARE REARRANGEMENT
• ASYMMETRIC 4+1 CYCLOADDITIONS
• ELECTRON-DEFICIENT ALKENES
• LIGHT PHOTOREDOX CATALYSIS
• DIAZO-COMPOUNDS
• 1,4-DICARBONYL COMPOUNDS
• CARBENE INSERTION
• N-TOSYLHYDRAZONES

Herein, a novel Cu-catalyzed four-component cascade reaction, which encompasses styrenes, diazo compounds, amines, and tert-butyl hydroperoxide (TBHP), was developed for the synthesis of beta-ester-gamma-amino ketones. Mechanistically, this transformation was initiated by the interception of an electrophilic Cu-based carbene with nucleophilic alpha-aminoalkyl radicals, followed by a radical cascade process and an ionic Kornblum-DeLaMare reaction. The methodology was also distinguished by its wide substrate scope, easily available starting materials, and operational simplicity.

• 出版日期2016
• 单位苏州大学