Water promoted enantioselective aldol Reaction by proline-cholesterol and -diosgenin based amphiphilic organocatalysts

被引：29

作者：

He, Ting ^{[1
]}

Li, Kun ^{[1
]}

Wu, Ming-Yu ^{[1
]}

Wu, Ming-Bo ^{[2
]}

Wang, Na ^{[1
]}

Pu, Lin ^{[1
]}

Yu, Xiao-Qi ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China

[2] Sichuan Univ, State Key Lab Oral Dis, Chengdu 610041, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 25期

基金：

美国国家科学基金会;

关键词：

Organocatalyst; Proline; Cholesterol; Diosgenin; Aldol reaction; ORGANIC-REACTIONS; CHIRAL CATALYSTS; ACID; ACCELERATION; ALDEHYDES; KETONES;

D O I：

10.1016/j.tet.2013.04.078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of proline-cholesterol and -diosgenin based amphiphilic organocatalysts were developed for the first time, and their catalytic activities for the enantioselective aldol reaction were investigated. The results indicated that water can significantly enhance the activity and stereoselectivity of the transformation via micelle formation. TEM and AFM analysis demonstrated that the diameter of the micelle particles ranged from 200 to 800 nm. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5136 / 5143

页数：8

共 53 条

[21] Recent efforts directed to the development of more sustainable asymmetric organocatalysis [J].

Hernandez, Jose G. ;

Juaristi, Eusebio .

CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5396-5409

[22] Amino acid catalyzed direct enantioselective formation of carbohydrates:: one-step de novo synthesis of ketoses [J].

Ibrahem, I ;

Córdova, A .

TETRAHEDRON LETTERS, 2005, 46 (19) :3363-3367

[23] Diastereoselectivities realized in the amino acid catalyzed aldol cyclizations of triketo acetonides of differing ring size [J].

Inomata, K ;

Barragué, M ;

Paquette, LA .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :533-539

[24] L-Proline/CoCl2-Catalyzed Highly Diastereo- and Enantioselective Direct Aldol Reactions [J].

Karmakar, Ananta ;

Maji, Tapan ;

Wittmann, Sebastian ;

Reiser, Oliver .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (39) :11024-11029

[25] Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update [J].

Li, CJ .

CHEMICAL REVIEWS, 2005, 105 (08) :3095-3165

[26]

Lindstrom U.M., 2007, ORGANIC REACTIONS WA

[27] Stereoselective organic reactions in water [J].

Lindström, UM .

CHEMICAL REVIEWS, 2002, 102 (08) :2751-2771

[28] Proline-catalyzed direct asymmetric aldol reactions [J].

List, B ;

Lerner, RA ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396

[29]

List B., 2004, MODERN ALDOL REACTIO, V1, P161

[30] Structural Effects on the Catalytic, Emulsifying, and Recycling Properties of Chiral Amphiphilic Dendritic Organocatalysts [J].

Lo, Chui-Man ;

Chow, Hak-Fun .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5181-5191

← 1 2 3 4 5 6 →