An efficient method for direct aldol reactions catalyzed by pyrrolidine/catechol - The influence of cooperation of Bronsted acidity and hydrogen-bond on the reaction

被引：12

作者：

Ji, CY

Peng, YG ^{[1
]}

Huang, CZ

Wang, N

Luo, Z

Jiang, YZ

机构：

[1] SW Normal Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2006年 / 246卷 / 1-2期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; pyrrolidine; catechol; bifunctional catalysis;

D O I：

10.1016/j.molcata.2005.10.022

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The aldol reactions of aromatic aldehydes with ketones catalyzed by pyrrolidine were accelerated by addition of a series of Bronsted acids to the reaction medium and found that the catechol was the most effective co-catalyst. The combination of pyrrolidine and catechol are very efficient for catalyzing the reaction to proceeding under mild conditions with high yield in short time. [GRAPHICS] (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：136 / 139

页数：4

共 37 条

[1] Origins of opposite absolute stereloselectivities in proline-catalyzed direct Mannich and aldol reactions [J].

Bahmanyar, S ;

Houk, KN .

ORGANIC LETTERS, 2003, 5 (08) :1249-1251

[2]

Benaglia M, 2002, ADV SYNTH CATAL, V344, P533, DOI 10.1002/1615-4169(200207)344:5<533::AID-ADSC533>3.0.CO

[3]

2-Y

[4]

BLOKZIJL W, 1993, ANGEW CHEM INT EDIT, V32, P1545, DOI 10.1002/anie.199315451

[5] Direct catalytic asymmetric aldol reactions of aldehydes [J].

Bogevig, A ;

Kumaragurubaran, N ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2002, (06) :620-621

[6]

Climent MJ, 2002, ADV SYNTH CATAL, V344, P1090, DOI 10.1002/1615-4169(200212)344:10<1090::AID-ADSC1090>3.0.CO

[7]

2-X

[8] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].

Córdova, A ;

Notz, W ;

Barbas, CF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303

[9] The chemistry of trichlorosilyl enolates. Aldol addition reactions of methyl ketones [J].

Denmark, SE ;

Stavenger, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (37) :8837-8847

[10] BASE-CATALYZED CONDENSATION OF ACETOPHENONE AND ISOBUTYRALDEHYDE - RE-EXAMINATION OF MONOMERIC AND DIMERIC ADDUCTS [J].

DILLING, WL ;

TEFERTIL.NB ;

HEESCHEN, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (25) :4159-4166

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