Asymmetric Synthesis of Cyclopenta[3,4]pyrroloindolones via N-Heterocyclic Carbene-Catalyzed Michael/AIdoI/Lactamization Cascade Reaction

被引：34

作者：

Yang, Yu-Jie ^{[1
]}

Ji, Yuanyuan ^{[1
]}

Qi, Liangliang ^{[1
]}

Wang, Guanjun ^{[1
]}

Hui, Xin-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 12期

关键词：

ACID COOPERATIVE CATALYSIS; HIGHLY STEREOSELECTIVE-SYNTHESIS; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ANNULATION REACTION; BRONSTED ACID; DIASTEREOSELECTIVE SYNTHESIS; INDOLE-DERIVATIVES; DOMINO REACTIONS; DELTA-LACTONES;

D O I：

10.1021/acs.orglett.7b01411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-heterocyclic carbene-catalyzed asymmetric Michael/aldol/lactamization cascade reaction of enals and indole-derived enones for the synthesis of functionalized cyclopenta[3,4]pyrroloindolones with four consecutive stereogenic centers has been achieved. The products were obtained in good yield with high diastereoselectivity and excellent enantioselectivity.

引用

页码：3271 / 3274

页数：4

共 83 条

[1] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[2] Bronsted Acid Catalyzed [3+2]-Cycloaddition of Cyclic Enamides with in Situ Generated 2-Methide-2H-indoles: Enantioselective Synthesis of Indolo[1,2-a]indoles [J].

Bera, Kalisankar ;

Schneider, Christoph .

ORGANIC LETTERS, 2016, 18 (21) :5660-5663

[3] Enantioselective Synthesis of Substituted δ-Lactones by Cooperative Oxidative N-Heterocyclic Carbene and Lewis Acid Catalysis [J].

Bera, Srikrishna ;

Daniliuc, Constantin G. ;

Studer, Armido .

ORGANIC LETTERS, 2015, 17 (20) :4940-4943

[4] NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins [J].

Bhunia, Anup ;

Patra, Atanu ;

Puranik, Vedavati G. ;

Biju, Akkattu T. .

ORGANIC LETTERS, 2013, 15 (07) :1756-1759

[5] Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction Partners [J].

Biju, Akkattu T. ;

Kuhl, Nadine ;

Glorius, Frank .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (11) :1182-1195

[6] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes [J].

Biju, Akkattu T. ;

Wurz, Nathalie E. ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5970-+

[7] Highly Stereoselective Synthesis of 1,2,3-Trisubstituted Indanes via Oxidative N-Heterocyclic Carbene-Catalyzed Cascades [J].

Biswas, Anup ;

De Sarkar, Suman ;

Froehlich, Roland ;

Studer, Armido .

ORGANIC LETTERS, 2011, 13 (18) :4966-4969

[8] Synthesis of Indolines, Indoles, and Benzopyrrolizidinones from Simple Aryl Azides [J].

Brucelle, Francois ;

Renaud, Philippe .

ORGANIC LETTERS, 2012, 14 (12) :3048-3051

[9] N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes [J].

Candish, Lisa ;

Levens, Alison ;

Lupton, David W. .

CHEMICAL SCIENCE, 2015, 6 (04) :2366-2370

[10] N-heterocyclic carbene cascade catalysis: Dual Bronsted/Lewis base rearrangement of cyclopropyl enol esters to dihydropyranones [J].

Candish, Lisa ;

Lupton, David W. .

CHEMICAL SCIENCE, 2012, 3 (02) :380-383

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