Ionic Liquid-Phase Organic Synthesis (IoLiPOS) Methodology Applied to Cross Aldol Reaction

被引：2

作者：

Hakkou, H. ^{[1
]}

Carrie, D. ^{[1
]}

Paquin, L. ^{[1
]}

Bazureau, J-P. ^{[1
]}

机构：

[1] Univ Rennes 1, Lab Sci Chim Rennes, UMR CNRS 6226, Grp Ingn Chim & Mol Vivant ICMV, F-35042 Rennes, France

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 47卷 / 03期

关键词：

Ionic Liquid; Aldol; Cyclopentanone; Aldol Reaction; MeONa;

D O I：

10.1134/S1070428011030079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cross aldol reaction in task-specific ionic liquids was developed. Ionic liquid-phase bound aldehyde reacted with various ketones (acetone, cyclopentanone, and butan-2-one) with L-proline as catalyst to afford various ionic liquid-phase supported aldols in yields ranging from 81 to 99%. Detachment of the aldol in MeOH was realized by transesterification using 15% of MeONa. The structure of intermediates in each step was verified by spectroscopic analysis.

引用

页码：371 / 373

页数：3

共 16 条

[1]

Bazureau J.P., 2006, MICROWAVE ORGANIC SY, P426

[2]

BESSON T, 2005, MICROWAVE ASSISTED O, pCH3

[3]

COMMARMOT R, 1985, Patent No. 25560529

[4] Direct asymmetric intermolecular aldol reactions catalyzed by amino acids and small peptides [J].

Cordova, Armando ;

Zou, Weibiao ;

Dziedzic, Pawel ;

Ibrahem, Ismail ;

Reyes, Efraim ;

Xu, Yongmei .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (20) :5383-5397

[5]

EDER U, 1971, J ORG CHEM, V10, P1615

[6] Ecofriendly fast synthesis of hydrophilic poly(ethyleneglycol)-ionic liquid matrices for liquid-phase organic synthesis [J].

Fraga-Dubreuil, J ;

Famelart, MH ;

Bazureau, JP .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2002, 6 (04) :374-378

[7] Grafted ionic liquid-phase-supported synthesis of small organic molecules [J].

Fraga-Dubreuil, J ;

Bazureau, JP .

TETRAHEDRON LETTERS, 2001, 42 (35) :6097-6100

[8] Structurally defined imidazolium-type ionic oligomers as soluble/solid support for peptide synthesis [J].

He, Xun ;

Chan, Tak Hang .

ORGANIC LETTERS, 2007, 9 (14) :2681-2684

[9] Asymmetric organocatalysis [J].

Houk, KN ;

List, B .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :487-487

[10] Functionalized imidazolium salts for task-specific ionic liquids and their applications [J].

Lee, SG .

CHEMICAL COMMUNICATIONS, 2006, (10) :1049-1063

← 1 2 →