Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

被引：111
|
作者：
Xing, Qi [1 ]
Chan, Chun-Ming [1 ]
Yeung, Yiu-Wai [1 ]
Yu, Wing-Yiu [1 ]
机构：
[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chem Biol & Drug Discovery, Hung Hom,Kowloon, Hong Kong, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 09期
关键词：
AMINATION; RUTHENIUM; CATALYST; FUNCTIONALIZATION; OXAZOLIDINONES; AZIRIDINATION; INSIGHT; BINDING; AZIDES; BONDS;
D O I：
10.1021/jacs.9b00535
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish gamma-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the C=C and C C bonds.
引用
收藏
页码：3849 / 3853
页数：5
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