Aqueous solutions of facial amphiphilic carbohydrates as sustainable media for organocatalyzed direct aldol reactions

被引：16
作者：
Bellomo, Ana [1 ,2 ]
Daniellou, Richard [1 ,2 ]
Plusquellec, Daniel [1 ,2 ]
机构：
[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6226, F-35708 Rennes 7, France
[2] Univ Europeenne Bretagne, Rennes, France
来源：
GREEN CHEMISTRY | 2012年 / 14卷 / 02期
关键词：
WATER;
D O I：
10.1039/c1gc16326d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The organocatalyzed direct aldol reaction was efficiently performed in aqueous solutions of facial amphiphilic carbohydrates with high diastereoselectivity and yield. Such sustainable media in addition with the use of 2% catalyst loading paves the way for the development of original ecofriendly procedures through non-covalent induction.
引用
收藏
页码：281 / 284
页数：4
相关论文
共 22 条
[1]   Immune versus natural selection: Antibody aldolases with enzymic rates but broader scope [J].
Barbas, CF ;
Heine, A ;
Zhong, GF ;
Hoffmann, T ;
Gramatikova, S ;
Bjornestedt, R ;
List, B ;
Anderson, J ;
Stura, EA ;
Wilson, IA ;
Lerner, RA .
SCIENCE, 1997, 278 (5346) :2085-2092
[2]   Allylation of cyclohexanones in aqueous media and influence of facial amphiphilic fructopyranosides [J].
Bellomo, Ana ;
Daniellou, Richard ;
Plusquellec, Daniel .
TETRAHEDRON LETTERS, 2010, 51 (38) :4934-4936
[3]   Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].
Brogan, Andrew P. ;
Dickerson, Tobin J. ;
Janda, Kim D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102
[4]   Organic Synthesis "On Water" [J].
Chanda, Arani ;
Fokin, Valery V. .
CHEMICAL REVIEWS, 2009, 109 (02) :725-748
[5]   Epoxidation of allylic alcohols in aqueous solutions of non surfactant amphiphilic sugars [J].
Denis, C ;
Misbahi, K ;
Kerbal, A ;
Ferrières, V ;
Plusquellec, D .
CHEMICAL COMMUNICATIONS, 2001, (23) :2460-2461
[6]   Highly regio- and stereoselective reductions of carbonyl compounds in aqueous glycosidic media [J].
Denis, C ;
Laignel, B ;
Plusquellec, D ;
LeMarouille, JY ;
Botrel, A .
TETRAHEDRON LETTERS, 1996, 37 (01) :53-56
[7]   Diastereospecific synthesis and amphiphilic properties of new alkyl β-D-fructopyranosides [J].
Ferrières, V ;
Benvegnu, T ;
Lefeuvre, M ;
Plusquellec, D ;
Mackenzie, G ;
Watson, MJ ;
Haley, JA ;
Goodby, JW ;
Pindak, R ;
Durbin, MK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (05) :951-959
[8]   Highly diastereo- and enantioselective direct aldol reactions in water [J].
Hayashi, Y ;
Sumiya, T ;
Takahashi, J ;
Gotoh, H ;
Urushima, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) :958-961
[9]   Highly efficient asymmetric direct stoichiometric aldol reactions on/in water [J].
Huang, Junmin ;
Zhang, Xiaotong ;
Armstrong, Daniel W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (47) :9073-9077
[10]   Asymmetric aldol reactions catalyzed by tryptophan in water [J].
Jiang, Zhaoqin ;
Liang, Zhian ;
Wu, Xiaoyu ;
Lu, Yixin .
CHEMICAL COMMUNICATIONS, 2006, (26) :2801-2803
123