Solvent-Free Selective Condensations Based on the Formation of the Olefinic (C=C) Bond Catalyzed by Organocatalyst

被引：4

作者：

Song, Heyuan ^{[1
,2
]}

Jin, Ronghua ^{[1
]}

Jin, Fuxiang ^{[1
]}

Kang, Meirong ^{[1
]}

Li, Zhen ^{[1
]}

Chen, Jing ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

[2] Univ Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

Catalysts | 2016年 / 6卷 / 07期

基金：

中国国家自然科学基金;

关键词：

aldol condensation; Knoevenagel condensation; organocatalysis; solvent-free condition; ketone; aldehyde; ASYMMETRIC ALDOL REACTIONS; IONIC LIQUID; KNOEVENAGEL REACTION; ALDEHYDES; KETONES; ALPHA;

D O I：

10.3390/catal6070106

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Pyrrolidine and its derivatives were used to catalyze aldol and Knoevenagel condensations for the formation of the olefinic (C = C) bond under solvent-free conditions. The 3-pyrrolidinamine showed high activity and afforded excellent yields of alpha, beta-unsaturated compounds. The aldol condensation of aromatic/heterocyclic aldehydes with ketones affords enones in high conversion (99.5%) and selectivity (92.7%). Good to excellent yields of alpha, beta-unsaturated compounds were obtained in the Knoevenagel condensation of aldehydes with methylene-activated substrates.

引用

页数：8

共 25 条

[1] Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[2] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
Bertelsen, Slren
Marigo, Mauro
Brandes, Sebastian
Diner, Peter
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
[3] Direct catalytic asymmetric aldol reactions of aldehydes
Bogevig, A
Kumaragurubaran, N
Jorgensen, KA
[J]. CHEMICAL COMMUNICATIONS, 2002, (06) : 620 - 621
[4] Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
Chimni, SS
Mahajan, D
[J]. TETRAHEDRON, 2005, 61 (21) : 5019 - 5025
[5] Direct organocatalytic aldol reactions in buffered aqueous media
Córdova, A
Notz, W
Barbas, CF
[J]. CHEMICAL COMMUNICATIONS, 2002, (24) : 3024 - 3025
[6] Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde
Córdova, A
Notz, W
Barbas, CF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) : 301 - 303
[7] Aqueous aldol catalysis by a nicotine metabolite
Dickerson, TJ
Janda, KD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) : 3220 - 3221
[8] Nornicotine aqueous aldol reactions: Synthetic and theoretical investigations into the origins of catalysis
Dickerson, TJ
Lovell, T
Meijler, MM
Noodleman, L
Janda, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) : 6603 - 6609
[9] TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES
EDER, U
SAUER, G
WEICHERT, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) : 496 - &
[10] The Knoevenagel reaction: analysis and recycling of the ionic liquid medium
Forbes, DC
Law, AM
Morrison, DW
[J]. TETRAHEDRON LETTERS, 2006, 47 (11) : 1699 - 1703

← 1 2 3 →