Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products

被引：13

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 LETTERS | 2013年 / 54卷 / 47期

基金：

中国国家自然科学基金;

关键词：

Aldol reaction; Organocatalysts; Chiral diamines; Configuration transformation; Enantioselectivity; ASYMMETRIC DIRECT ALDOL; DIRECT SYN-ALDOL; ORGANIC-REACTIONS; L-PROLINAMIDE; EFFICIENT; ACID; DESIGN; ORGANOCATALYSTS; MICHAEL; KETONES;

D O I：

10.1016/j.tetlet.2013.09.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral derivatives of trans-1,2-diaminocyclohexane with different N,N-dialkyl groups in well-defined orientations have been synthesized, and applied as catalysts for the asymmetric aldol reaction between a variety of aldehydes and ketones. Enantiomeric catalyst 1j catalyzed the reaction in ethanol and provided excellent diastereoselectivity and enantioselectivity. Significantly, simple replacement of organic solvents with water switched the products of the aldol reactions from anti to syn configuration. Such catalytic reactions led to the products with anti to syn diastereoselectivity up to 99:1 in ethanol, while in water gave the products with syn to anti diastereoselectivity up to 99:1. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：6358 / 6362

页数：5

共 60 条

[1] Asymmetric glycolate aldol reactions using cinchonium phase-transfer catalysts
Andrus, MB
Liu, J
Ye, ZF
Cannon, JF
[J]. ORGANIC LETTERS, 2005, 7 (18) : 3861 - 3864
[2] [Anonymous], J AM CHEM SOC
[3] Bach T., 1994, ANGEW CHEM, V106, P433, DOI 10.1002/ange.19941060406
[4] Benaglia M, 2001, ADV SYNTH CATAL, V343, P171, DOI 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.3.CO
[5] 2-V
[6] Organocatalysis-after the gold rush
Bertelsen, Soren
Jorgensen, Karl Anker
[J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189
[7] HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER
BRESLOW, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) : 159 - 164
[8] Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water
Chen, Guodong
Fu, Xiangkai
Li, Chao
Wu, Chuanlong
Miao, Qiang
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 702 : 19 - 26
[9] Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions
Chen, JR
Lu, HH
Li, XY
Cheng, L
Wan, J
Xiao, WJ
[J]. ORGANIC LETTERS, 2005, 7 (20) : 4543 - 4545
[10] Supramolecular-Directed Chiral Induction in Biaryl Derivatives
Etxebarria, J.
Degenbeck, H.
Felten, A. -S.
Serres, S.
Nieto, N.
Vidal-Ferran, A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) : 8794 - 8797

← 1 2 3 4 5 6 →