Direct enantioselective aldol reactions catalyzed by a proline-thiourea host-guest complex

被引：99

作者：

Reis, Oemer ^{[1
]}

Eymur, Serkan ^{[1
]}

Reis, Barbaros ^{[1
]}

Demir, Ayhan S. ^{[1
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

来源：

CHEMICAL COMMUNICATIONS | 2009年 / 09期

关键词：

DYNAMIC KINETIC RESOLUTION; BAYLIS-HILLMAN REACTION; ASYMMETRIC ORGANOCATALYSIS; METAL-FREE; WATER; ACID; ADDITIVES; ALDEHYDES; PREDICTIONS; DERIVATIVES;

D O I：

10.1039/b817474a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Proline-thiourea host-guest complex-catalyzed direct enantioselective aldol reactions have been developed, in which the catalytic activities were evaluated in the direct asymmetric aldol reactions of various aromatic aldehydes and cyclohexanone.

引用

页码：1088 / 1090

页数：3

共 42 条

[1] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[2] Primary amine catalyzed direct asymmetric aldol reaction assisted by water [J].

Amedjkouh, M .

TETRAHEDRON-ASYMMETRY, 2005, 16 (08) :1411-1414

[3] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].

Bahmanyar, S ;

Houk, KN ;

Martin, HJ ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479

[4] Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions [J].

Berkessel, A ;

Koch, B ;

Lex, J .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1141-1146

[5]

CASAS CP, 2008, J ORG CHEM, V73, P2275

[6] Self-assembly of organocatalysts: Fine-tuning organocatalytic reactions [J].

Clarke, Matthew L. ;

Fuentes, Jose A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :930-933

[7] Computational evidence for the enamine mechanism of intramolecular Aldol reactions catalyzed by proline [J].

Clemente, FR ;

Houk, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5766-5768

[8] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[9] The small peptide-catalyzed direct asymmetric aldol reaction in water [J].

Dziedzic, P ;

Zou, WB ;

Háfren, J ;

Córdova, A .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) :38-40

[10] 5-(Pyrrolidine-2-yl)tetrazole: Rationale for the increased reactivity of the tetrazole analogue of proline in organocatalyzed aldol reactions [J].

Hartikka, A ;

Arvidsson, PI .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4287-4295

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