A catalytic aldol reaction and condensation through in situ boron "Ate" complex enolate generation in water

被引：49

作者：

Aelvoet, Karel ^{[1
]}

Batsanov, Andrei S. ^{[1
]}

Blatch, Alexandrea J. ^{[1
]}

Grosjean, Christophe ^{[1
]}

Patrick, Leonard G. F. ^{[1
]}

Smethurst, Christian A. ^{[2
]}

Whiting, Andrew ^{[1
]}

机构：

[1] Univ Durham, Sci Labs, Dept Chem, Durham DH1 3QZ, England

[2] GlaxoSmithKline, Discovery Res Syst Chem, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 04期

关键词：

aldol reaction; bifunctional catalysts; boron; homogeneous catalysis; selectivity;

D O I：

10.1002/anie.200704293

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Cooperation is key: N-Butyl-1-benzimidazole- 2-phenylboronic acid hydroxide complex catalyzes the aldol condensation and aldol addition between hydroxyacetone or acetone, and different aldehydes in water. The catalytic activity results from cooperative interactions between the boronate complex and the imidazole function. Aldol condensation gives the unsaturated methyl ketones of acetone, whereas aldol addition predominates with hydroxyacetone. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：768 / 770

页数：3

共 36 条

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] To catalyze or not to catalyze? Insight into direct amide bond formation from amines and carboxylic acids under thermal and catalyzed conditions [J].

Arnold, Kenny ;

Davies, Bryan ;

Giles, Richard L. ;

Grosjean, Christophe ;

Smith, Gillian E. ;

Whiting, Andrew .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :813-820

[3] Enantioselective catalysis in water: Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol) [J].

Benaglia, M ;

Cinquini, M ;

Cozzi, F ;

Celentano, G .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (22) :3401-3407

[4] Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives [J].

Blatch, Alexandrea J. ;

Chetina, Olga V. ;

Howard, Judith A. K. ;

Patrick, Leonard G. F. ;

Smethurst, Christian A. ;

Whiting, Andrew .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3297-3302

[5] A proline-catalyzed asymmetric Robinson annulation reaction [J].

Bui, T ;

Barbas, CF .

TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954

[6] Organocatalytic asymmetric assembly reactions:: One-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates [J].

Chowdari, NS ;

Ramachary, DB ;

Barbas, CF .

ORGANIC LETTERS, 2003, 5 (10) :1685-1688

[7] Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts:: 2-N,N-diisopropylaminophenylboronate derivatives [J].

Coghlan, SW ;

Giles, RL ;

Howard, JAK ;

Patrick, LGF ;

Probert, MR ;

Smith, GE ;

Whiting, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (21-22) :4784-4793

[8] Zn-proline catalyzed direct aldol reaction in aqueous media [J].

Darbre, T ;

Machuqueiro, M .

CHEMICAL COMMUNICATIONS, 2003, (09) :1090-1091

[9] Aqueous aldol catalysis by a nicotine metabolite [J].

Dickerson, TJ ;

Janda, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3220-3221

[10] Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts:: 1-N,N-dimethylamino-8-borononaphthalene derivatives [J].

Giles, RL ;

Howard, JAK ;

Patrick, LGF ;

Probert, MR ;

Smith, GE ;

Whiting, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) :257-262

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