Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine

被引：17

作者：

Li, Lei ^{[1
,2
]}

Gou, Shaohua ^{[1
,2
,3
]}

Liu, Fei ^{[1
,2
]}

机构：

[1] Southeast Univ, Pharmaceut Res Ctr, Nanjing 211189, Jiangsu, Peoples R China

[2] Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Jiangsu, Peoples R China

[3] Southeast Univ, Jiangsu Prov Hitech Key Lab Biomed Res, Nanjing 211189, Jiangsu, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2014年 / 25卷 / 02期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; UNACTIVATED KETONES; ARYL ALDEHYDES; AQUEOUS-MEDIUM; L-PROLINAMIDE; ORGANOCATALYSTS; WATER; ISATINS; ACETALDEHYDE; DESIGN;

D O I：

10.1016/j.tetasy.2013.11.017

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective organocatalytic direct aldol reactions of ketones with various aldehydes were developed by using chiral 1,2-cyclohexanediamine COACH) based multifunctional ligands via a noncovalent catalysis mechanism. By using a catalyst, we also obtained functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields and with good to excellent enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：193 / 197

页数：5

共 58 条

[21] Attractive noncovalent interactions in asymmetric catalysis: Links between enzymes and small molecule catalysts
Knowles, Robert R.
Jacobsen, Eric N.
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (48) : 20678 - 20685
[22] Direct asymmetric aldol reaction of aryl ketones with aryl aldehydes catalyzed by chiral BINOL-derived zincate catalyst
Li, Hong
Da, Chao-Shan
Xiao, Yu-Hua
Li, Xiao
Su, Ya-Ning
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) : 7398 - 7401
[23] Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products
Li, Lei
Gou, Shaohua
Liu, Fei
[J]. TETRAHEDRON LETTERS, 2013, 54 (47) : 6358 - 6362
[24] Proline-catalyzed direct asymmetric aldol reactions
List, B
Lerner, RA
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) : 2395 - 2396
[25] Chiral 1,2-diaminocyclohexane as organocatalyst for enantioselective aldol reaction
Liu, Yi
Wang, Junfeng
Sun, Qi
Li, Runtao
[J]. TETRAHEDRON LETTERS, 2011, 52 (28) : 3584 - 3587
[26] A simple primary-tertiary diamine-Bronsted acid catalyst for asymmetric direct Aldol reactions of linear aliphatic ketones
Luo, Sanzhong
Xu, Hui
Li, Jiuyuan
Zhang, Long
Cheng, Jin-Pei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3074 - +
[27] Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins
Luppi, G
Cozzi, PG
Monari, M
Kaptein, B
Broxterman, QB
Tomasini, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) : 7418 - 7421
[28] Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst
Lygo, Barry
Davison, Christopher
Evans, Timothy
Gilks, James A. R.
Leonard, John
Roy, Claude-Eric
[J]. TETRAHEDRON, 2011, 67 (52) : 10164 - 10170
[29] Machajewski TD, 2000, ANGEW CHEM INT EDIT, V39, P1352, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1352::AID-ANIE1352>3.0.CO
[30] 2-J

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