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

被引：106

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

页码：3849 / 3853

页数：5

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