Visible-Light-Activated Catalytic Enantioselective β-Alkylation of α, β-Unsaturated 2-Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs

被引：57

作者：

de Assis, Francisco F. ^{[1
,2
]}

Huang, Xiaoqiang ^{[2
]}

Akiyama, Midori ^{[3
]}

Pilli, Ronaldo A. ^{[1
]}

Meggers, Eric ^{[2
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil

[2] Philipps Univ Marburg, Fachbereich Chem, Hans Meerwein Str 4, D-35043 Marburg, Germany

[3] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Tokyo, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期

基金：

巴西圣保罗研究基金会;

关键词：

LEWIS-ACID CATALYSIS; COUPLED ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; CONJUGATE ADDITION; FUNCTIONALIZATION; 4-ALKYL-1,4-DIHYDROPYRIDINES; DEBROMINATION; GENERATION; REAGENTS; KETONES;

D O I：

10.1021/acs.joc.8b01588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical method for the enantioselective beta-functionalization of alpha, beta-unsaturated 2-acyl imidazoles is described. The method uses a previously devised chiral-at-metal rhodium catalyst (Lambda-RhS, 4 mol %) along with Hantzsch ester derivatives as alkyl radical sources. The rhodium complex exerts a dual role as the visible-light-absorbing unit upon substrate binding and as the asymmetric catalyst. The method provides up to quantitative yields with excellent enantioselectivities up to 98% ee and can be classified as a redox-neutral, electron-transfer-catalyzed reaction.

引用

页码：10922 / 10932

页数：11

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