Enantioselective Synthesis of Functionalized Pyrazoles by NHC-Catalyzed Reaction of Pyrazolones with α,β-Unsaturated Aldehydes

被引：101

作者：

Yetra, Santhivardhana Reddy ^{[1
]}

Mondal, Santigopal ^{[1
]}

Suresh, Eringathodi ^{[2
,3
]}

Biju, Akkattu T. ^{[1
]}

机构：

[1] CSIR Natl Chem Lab CSIR NCL, Div Organ Chem, Pune 411008, Maharashtra, India

[2] CSIR Cent Salt & Marine Chem Res Inst, Analyt Dept, Bhavnagar 364002, Gujarat, India

[3] CSIR Cent Salt & Marine Chem Res Inst, Centralized Instrument Facil, Bhavnagar 364002, Gujarat, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 06期

关键词：

HETEROCYCLIC CARBENE CATALYSIS; ACYL AZOLIUMS; MICHAEL ADDITION; 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS; CASCADE REACTION; MODIFIED ENALS; BETA-LACTONES; ANNULATION; ESTERS;

D O I：

10.1021/acs.orglett.5b00293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The N-heterocyclic carbene (NHC)-organocatalyzed enantioselective annulation reaction of pyrazolones with alpha,beta-unsaturated aldehydes proceeding via the chiral alpha,beta-unsaturated acyl azolium intermediates under oxidative conditions is presented. The reaction afforded dihydropyranone-fused pyrazoles in moderate to good yields and good er values under operationally simple and base-free conditions.

引用

页码：1417 / 1420

页数：4

共 62 条

[1] Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid [J].

Bera, Srikrishna ;

Samanta, Ramesh C. ;

Daniliuc, Constantin G. ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9622-9626

[2]

Bertheleme N., 2007, [No title captured], Patent No. [PCT/EP2007061794, 2007061794, PCT/EP2007/061794]

[3]

Bradley DM, PCT/EP2007/061794, Patent No. [2008053031, PCT/WO2008053031A1]

[4] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[5]

Brune K., 1997, Acute Pain, V1, P33, DOI DOI 10.1016/S1366-0071(97)80033-2

[6] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[7] Enantioselective All-Carbon (4+2) Annulation by N-Heterocyclic Carbene Catalysis [J].

Candish, Lisa ;

Levens, Alison ;

Lupton, David W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) :14397-14400

[8] N-Heterocyclic Carbene-Catalyzed Ireland-Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones [J].

Candish, Lisa ;

Lupton, David W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) :58-61

[9] NHC Organocatalytic Formal LUMO Activation of α,β-Unsaturated Esters for Reaction with Enamides [J].

Cheng, Jiajia ;

Huang, Zhijian ;

Chi, Yonggui Robin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) :8592-8596

[10]

Chiang PC, 2011, RSC CATAL SER, P399

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