N-Heterocyclic Carbene Catalyzed Highly Chemoselective Intermolecular Crossed Acyloin Condensation of Aromatic Aldehydes with Trifluoroacetaldehyde Ethyl Hemiacetal

被引：32

作者：

Ramanjaneyulu, Bandaru T. ^{[1
]}

Mahesh, Sriram ^{[1
]}

Anand, Ramasamy Vijaya ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Mohali 140306, Punjab, India

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 01期

关键词：

INTRAMOLECULAR STETTER REACTION; KETONE BENZOIN REACTIONS; ALPHA-TRIFLUOROMETHYLATED ALCOHOLS; DIRECT ALDOL REACTION; ENE-TYPE REACTION; MEDICINAL CHEMISTRY; TRIAZOLIUM SALTS; PRACTICAL SYNTHESIS; FORMING REACTIONS; THIAZOLIUM SALT;

D O I：

10.1021/ol502581b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly chemoselective intermolecular crossed acyloin condensation between aromatic aldehydes and trifluoroacetaldehyde ethyl hemiacetal has been developed under mild reaction conditions using N-heterocyclic carbene as a catalyst. A wide range of aromatic aldehydes bearing electron-withdrawing and -donating substituents underwent a smooth transformation to their corresponding trifluoromethyl containing acyloin derivatives in moderate to good yields.

引用

页码：6 / 9

页数：4

共 84 条

[1] Efficient Synthesis of γ-Keto Sulfones by NHC-Catalyzed Intermolecular Stetter Reaction [J].

Bhunia, Anup ;

Yetra, Santhivardhana Reddy ;

Bhojgude, Sachin Suresh ;

Biju, Akkattu T. .

ORGANIC LETTERS, 2012, 14 (11) :2830-2833

[2] 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

[3] 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

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

Bugaut, Xavier ;

Glorius, Frank .

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

[5] Solvent-Free Stereoselective Synthesis of (E)-Trifluoromethyl Imines and Hydrazones [J].

Carroccia, Laura ;

Fioravanti, Stefania ;

Pellacani, Lucio ;

Tardella, Paolo A. .

SYNTHESIS-STUTTGART, 2010, (23) :4096-4100

[6]

Chiang P.-C., 2011, TCI MAIL, V149, P2

[7] New developments in the asymmetric Stetter reaction [J].

Christmann, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2632-2634

[8] The Catalytic Asymmetric Intramolecular Stetter Reaction [J].

de Alaniz, Javier Read ;

Rovis, Tomislav .

SYNLETT, 2009, (08) :1189-1207

[9] Catalytic Asymmetric Intermolecular Stetter Reaction of Enals with Nitroalkenes: Enhancement of Catalytic Efficiency through Bifunctional Additives [J].

DiRocco, Daniel A. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) :10402-10405

[10] Catalytic Asymmetric Intermolecular Stetter Reaction of Heterocyclic Aldehydes with Nitroalkenes: Backbone Fluorination Improves Selectivity [J].

DiRocco, Daniel A. ;

Oberg, Kevin M. ;

Dalton, Derek M. ;

Rovis, Tomislav .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10872-+

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