Rh2(II)-Catalyzed Selective C(sp3)-H Bond Electrophilic Amination of Aryl Azide-Tethered 1,3-Dicarbonyl Compounds

被引：4
|
作者：
Donthoju, Ashok [1 ,2 ]
Phanindrudu, Mandalaparthi [1 ]
Ellandula, Sushma [1 ]
Lal, Malavath Ratan [1 ]
Nanubolu, Jagadeesh Babu [2 ,3 ]
Chegondi, Rambabu [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
[3] CSIR Indian Inst Chem Technol CSIR IICT, Dept Analyt & Struct Chem, Hyderabad 500007, India
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 41期
关键词：
ALPHA-AMINATION; FUNCTIONALIZATION; DERIVATIVES; CATALYSTS; ROUTE;
D O I：
10.1021/acs.orglett.3c03067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the accomplishment of Rh2(II)-catalyzed intramolecular amination of aryl azide-tethered 1,3-dicarbonyls to access privileged heterocyclic scaffolds with exclusive diastereoselectivity under simple reaction conditions. This method also allows an unconventional direct alpha-amination at electron-deficient C-(sp3)-H bonds of aryl azide-tethered 1,3-diketones to afford fused 2-azatricyclo-[4.4.0.02,8]-decanones and 2,2-disubstituted indolines, which are present in several biologically active alkaloids. Kinetic isotope experiments revealed that the nucleophilic addition of enol pi-bonds on the transient electrophilic rhodium-nitrenoid intermediate enables C-N bond formation.
引用
收藏
页码：7589 / 7594
页数：6
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