A Cu-catalyzed four-component cascade reaction to construct β-ester-γ-amino ketones. Issue 23 (24th May 2016)

• Record Type: Journal Article
• Authors: Ling, Jiayue; Zhang, Jie; Zhao, Yanwei; Xu, Yudong; Wang, Hanghang; Lv, Yuanzheng; Ji, Meishan; Ma, Liang; Ma, Meihua; Wan, Xiaobing
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 23(2016)
• Page Start: 5310
• Page End: 5316
• Publication Date: 2016-05-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00873a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Herein, a novel Cu-catalyzed four-component cascade reaction, which encompasses styrenes, diazo reagents, amines, and tert -butyl hydroperoxide (TBHP), was well developed toward β-ester-γ-amino ketones, which showed high chemoselectivity. Abstract : 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 β-ester-γ-amino ketones. Mechanistically, this transformation was initiated by the interception of an electrophilic Cu-based carbene with nucleophilic α-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.