N-Heterocyclic carbene-catalyzed hydroacylation of isatins with aldehydes: access to 3-acyloxy-1,3-dihydro-2H-indol-2-ones

被引：24

作者：

Du, Ding ^{[1
]}

Lu, Yingyan ^{[1
]}

Jin, Jianlin ^{[1
]}

Tang, Weifang ^{[1
]}

Lu, Tao ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, Nanjing 210009, Peoples R China

[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 210009, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 39期

基金：

高等学校博士学科点专项科研基金; 中国国家自然科学基金;

关键词：

N-Heterocyclic carbenes; Organocatalysis; Hydroacylation; Isatins; Aldehydes; FORMYLCYCLOPROPANE 1,1-DIESTERS; INTERMOLECULAR HYDROACYLATION; ENANTIOSELECTIVE SYNTHESIS; COMPLEXES; SALICYLALDEHYDES; REARRANGEMENT; PRECURSORS; THIAZOLIUM; OXIDATION; REAGENTS;

D O I：

10.1016/j.tet.2011.07.075

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-heterocyclic carbene-catalyzed hydroacylation of isatins with aldehydes has been described. This process offers a highly efficient and atom-ecomonical access to 3-acyloxy-1,3-dihydro-2H-indol-2-ones in good to excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：7557 / 7562

页数：6

共 65 条

[1] Palladium-Catalyzed Enantioselective Ene and Aldol Reactions with Isatins, Keto Esters, and Diketones: Reliable Approach to Chiral Tertiary Alcohols [J].

Aikawa, Kohsuke ;

Mimura, Shunsuke ;

Numata, Yukinobu ;

Mikami, Koichi .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (01) :62-65

[2] CINNOLINES .28. THE NATURE OF THE C(3)-POSITION .1. THE BER-BOSSEL SYNTHESIS OF 3-HYDROXYCINNOLINE [J].

ALFORD, EJ ;

SCHOFIELD, K .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUN) :2102-2108

[3] Formation and stability of N-heterocyclic carbenes in water:: The carbon acid pKa of imidazollum cations in aqueous solution [J].

Amyes, TL ;

Diver, ST ;

Richard, JP ;

Rivas, FM ;

Toth, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4366-4374

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

Bandini, Marco ;

Eichholzer, Astrid .

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

[5]

Banerji A, 1998, J INDIAN CHEM SOC, V75, P698

[6] HOMOGENEOUS CATALYSIS - CATALYTIC INTRAMOLECULAR CONVERSION OF 1,4-DIALDEHYDES TO GAMMA-LACTONES [J].

BERGENS, SH ;

FAIRLIE, DP ;

BOSNICH, B .

ORGANOMETALLICS, 1990, 9 (03) :566-571

[7] Intermolecular N-Heterocyclic Carbene Catalyzed Hydroacylation of Arynes [J].

Biju, Akkattu T. ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) :9761-9764

[8] 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-+

[9] Asymmetric catalysis. A comparative study of the mechanisms of intramolecular hydroacylation and hydrosilation [J].

Bosnich, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (10) :667-674

[10]

BRAJE W, 2009, Patent No. 2009083559

← 1 2 3 4 5 6 7 →