NHC-Catalyzed O-Selective Addition of Nitrosoarenes with Aldehydes

被引：10

作者：

Wang, Gang ^{[1
]}

Chen, Xia ^{[1
]}

Zhang, Yi ^{[1
,2
]}

Yao, Weijun ^{[1
]}

Ma, Cheng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Zhejiang Tianyu Pharmaceut Co Ltd, Taizhou, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

ALPHA-KETOGLUTARATE DEHYDROGENASE; HETEROCYCLIC CARBENE CATALYSIS; HYDROXAMIC ACID PRODUCTION; OXIDATIVE ESTERIFICATION; GAMMA-BUTYROLACTONES; CARBONYL-COMPOUNDS; ACTIVE-SITE; ORGANOCATALYSIS; AMINOXYLATION; INTERMEDIATE;

D O I：

10.1021/ol4012458

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An NHC-catalyzed O-selective addition of nitrosoarenes with aldehydes probably upon a dual-activation mode was developed, generating a variety of O-acyl hydroxylamines without any detectable competing amidation byproducts.

引用

页码：3066 / 3069

页数：4

共 48 条

[1] 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

[2] 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-+

[3] The Nitrosocarbonyl Hetero-Diels-Alder Reaction as a Useful Tool for Organic Syntheses [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) :5629-5646

[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] The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].

Brown, SP ;

Brochu, MP ;

Sinz, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809

[6] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[7] N,O-Diacyl-4-benzoyl-N-phenylhydroxylamines as photoinduced DNA cleaving agents [J].

Chowdhury, Nilanjana ;

Dutta, Sansa ;

Nishitha, Boda ;

Dasgupta, Swagata ;

Singh, N. D. Pradeep .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (18) :5414-5417

[8] HYDROXAMIC ACID PRODUCTION AND ACTIVE-SITE INDUCED BAMBERGER REARRANGEMENT FROM THE ACTION OF ALPHA-KETOGLUTARATE DEHYDROGENASE ON 4-CHLORONITROSOBENZENE [J].

CORBETT, MD ;

CORBETT, BR ;

DOERGE, DR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (02) :345-350

[9] HYDROXAMIC ACID PRODUCTION BY ALPHA-KETOGLUTARATE DEHYDROGENASE .2. EVIDENCE FOR AN ELECTROPHILIC REACTION INTERMEDIATE AT THE ENZYME ACTIVE-SITE [J].

CORBETT, MD ;

DOERGE, DR ;

CORBETT, BR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (04) :765-769

[10] Catalysis with N-Heterocyclic Carbenes under Oxidative Conditions [J].

De Sarkar, Suman ;

Biswas, Anup ;

Samanta, Ramesh C. ;

Studer, Armido .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (15) :4664-4678

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