Aqua-organocatalyzed direct asymmetric aldol reaction with acyclic amino acids and organic bases with control of diastereo- and enantioselectivity

被引：65

作者：

Amedjkouh, Mohamed ^{[1
]}

机构：

[1] Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 03期

基金：

瑞典研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2007.01.025

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An effective aqua-organocatalytic direct aldol reaction is described. Aromatic amino acids can be a bifunctional catalyst system, which demonstrate excellent reactivity, diastereoselectivity, and enantioselectivity (up to 96% ee) in water without the addition of organic solvents. Furthermore, the present study demonstrates that both diastereo and enantioselectivity can be easily modulated by the appropriate combination of an organocatalyst together with an organic base as a co-catalyst. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：390 / 395

页数：6

共 45 条

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

Amedjkouh, M .

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

[2] 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

[3] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164

[4] Direct organocatalytic aldol reactions in buffered aqueous media [J].

Córdova, A ;

Notz, W ;

Barbas, CF .

CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025

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

Darbre, T ;

Machuqueiro, M .

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

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

Dickerson, TJ ;

Janda, KD .

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

[7] Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction:: towards syn selectivity in the presence of Lewis bases [J].

Diner, Peter ;

Amedjkouh, Mohamed .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2091-2096

[8] Cation-pi interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp [J].

Dougherty, DA .

SCIENCE, 1996, 271 (5246) :163-168

[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] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].

EDER, U ;

SAUER, G ;

WEICHERT, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&

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