One-Pot Decarboxylative Acylation of N-, O-, S-Nucleophiles and Peptides with 2,2-Disubstituted Malonic Acids

被引：7

作者：

Lebedyeva, Iryna O. ^{[1
,2
]}

Biswas, Suvendu ^{[1
]}

Goncalves, Kevin ^{[1
]}

Sileno, Sean M. ^{[1
]}

Jackson, Ashton R. ^{[1
]}

Patel, Kunal ^{[1
]}

Steel, Peter J. ^{[3
]}

Katritzky, Alan R. ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Georgia Regents Univ, Dept Chem & Phys, Augusta, GA 30912 USA

[3] Univ Canterbury, Dept Chem, Christchurch 8140, New Zealand

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 37期

关键词：

acylation; cleavage reactions; conjugates; decarboxylation; peptides; BENZOIC-ACIDS; ALCALIGENES-BRONCHISEPTICUS; ASYMMETRIC DECARBOXYLATION; RADICAL CONDITIONS; CARBOXYLIC-ACIDS; ARYL HALIDES; PROTODECARBOXYLATION; ARYLATION; OXALATE;

D O I：

10.1002/chem.201403529

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.

引用

页码：11695 / 11698

页数：4

共 25 条

[1]

Aldabalde V., 2011, Open J. Phys. Chem, V1, P85

[2] SILVER(I)-CATALYZED OXIDATIVE DECARBOXYLATION OF ACIDS BY PEROXYDISULFATE - ROLE OF SILVER(II) [J].

ANDERSON, JM ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1651-&

[3]

[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.200300579

[4] Direct ortho-Arylation of ortho-Substituted Benzoic Acids: Overriding Pd-Catalyzed Protodecarboxylation [J].

Arroniz, Carlos ;

Ironmonger, Alan ;

Rassias, Gerry ;

Larrosa, Igor .

ORGANIC LETTERS, 2013, 15 (04) :910-913

[5] Enantioselective catalysis .100. Decarboxylation of malonic acids in the presence of copper(I) compounds - Not a copper(I) catalysis but a base effect [J].

Brunner, H ;

Muller, J ;

Spitzer, J .

MONATSHEFTE FUR CHEMIE, 1996, 127 (8-9) :845-858

[6]

Calí P, 2002, SYNTHESIS-STUTTGART, P63

[7] Synthesis of new amphiphilic dendrons bearing aliphatic hydrocarbon surface sectors and a monocarboxylic or dicarboxylic acid focal point [J].

Chow, HF ;

Ng, KF ;

Wang, ZY ;

Wong, CH ;

Luk, T ;

Lo, CM ;

Yang, YY .

ORGANIC LETTERS, 2006, 8 (03) :471-474

[8] THE DECARBOXYLATION OF MALONIC ACID IN ACID MEDIA [J].

CLARK, LW .

JOURNAL OF PHYSICAL CHEMISTRY, 1960, 64 (01) :41-43

[9] THE MECHANISM OF THE DECARBOXYLATION OF ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED MALONIC ACID DERIVATIVES AND THE COURSE OF DECARBOXYLATIVE CONDENSATION REACTIONS IN PYRIDINE [J].

COREY, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5897-5905

[10] Decarboxylative Carbon-Carbon Bond-Forming Transformations of (Hetero)aromatic Carboxylic Acids [J].

Cornella, Josep ;

Larrosa, Igor .

SYNTHESIS-STUTTGART, 2012, 44 (05) :653-676

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