Regio-and Enantioselective Synthesis of N-Allylindoles by Iridium-Catalyzed Allylic Amination/Transition-Metal-Catalyzed Cyclization Reactions

被引：40

作者：

Ye, Ke-Yin ^{[1
]}

Dai, Li-Xin ^{[1
]}

You, Shu-Li ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 11期

基金：

中国国家自然科学基金;

关键词：

allylic substitution; N-allylindole; asymmetric catalysis; enantioselectivity; iridium; FRIEDEL-CRAFTS ALKYLATION; PHOSPHORAMIDITE LIGANDS; 2,3-DISUBSTITUTED INDOLES; EFFICIENT SYNTHESIS; AROMATIC-AMINES; ACID CATALYSIS; FUNCTIONALIZATION; DERIVATIVES; ALLYLATION; SUBSTITUTIONS;

D O I：

10.1002/chem.201400026

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Regio- and enantioselective synthesis of N-allylindoles was realized through an iridium-catalyzed asymmetric allylic amination reaction with 2-alkynylanilines and subsequent transition-metal-catalyzed cyclization reactions. The highly enantioenriched allylic amines prepared from Ir-catalysis were treated with catalytic amount of NaAuCl(4)2H(2)O or PdCl2 providing various substituted N-allylindoles in excellent yields and enantioselectivities.

引用

页码：3040 / 3044

页数：5

共 128 条

[1] Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].

Ackermann, Lutz .

SYNLETT, 2007, (04) :507-526

[2] A General Synthesis of Alkenyl-Substituted Benzofurans, Indoles, and Isoquinolones by Cascade Palladium-Catalyzed Heterocyclization/Oxidative Heck Coupling [J].

Alvarez, Rosana ;

Martinez, Claudio ;

Madich, Youssef ;

Denis, J. Gabriel ;

Aurrecoechea, Jose M. ;

de Lera, Angel R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) :12746-12753

[3]

[Anonymous], 2008, ANGEW CHEM-GER EDIT

[4]

[Anonymous], 2004, ANGEW CHEM, V116, P560

[5]

[Anonymous], ANGEW CHEM

[6] Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles [J].

Arcadi, A ;

Bianchi, G ;

Marinelli, F .

SYNTHESIS-STUTTGART, 2004, (04) :610-618

[7] One-Pot Gold-Catalyzed Aminofluorination of Unprotected 2-Alkynylanilines [J].

Arcadi, Antonio ;

Pietropaolo, Emanuela ;

Alvino, Antonello ;

Michelet, Veronique .

ORGANIC LETTERS, 2013, 15 (11) :2766-2769

[8]

Atzrodt J., 2007, ANGEW CHEM, V119, P7890

[9] The renaissance of H/D exchange [J].

Atzrodt, Jens ;

Derdau, Volker ;

Fey, Thorsten ;

Zimmermann, Jochen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7744-7765

[10] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].

Austin, JF ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173

← 1 2 3 4 5 6 7 8 9 10 →