Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction

被引：0

作者：

Gao Jun-long ^{[1
]}

Zheng Liang-yu ^{[2
]}

Zhang Suo-qin ^{[1
]}

Zhang Xin-min ^{[1
]}

Sun Guo-dong ^{[1
]}

Qin Lin ^{[1
]}

Li Yao-xian ^{[1
]}

Liu Qing-wen ^{[1
]}

Li Xiao-bo ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, Changchun 130021, Peoples R China

[2] Jilin Univ, Key Lab Mol Enzymol & Engn, Minist Educ, Changchun 130021, Peoples R China

来源：

CHEMICAL RESEARCH IN CHINESE UNIVERSITIES | 2010年 / 26卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Proline-based dipeptide; Aldol reaction; Enantioselectivity; ASYMMETRIC ALDOL; ENAMINE CATALYSIS; ALDEHYDES; ACID; DIETHYLZINC; STRATEGY; KETONES; DESIGN;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of proline-based amino pyridine dipeptide organocatalysts was synthesized and applied in direct asymmetric intermolecular aldol reaction. These catalysts showed good solubility in organic solvents, good yields (73%-97%) and enantioselectivitives(74%-94%). Among them, dipeptide organocatalyst(2) was found to be the most efficient one for the asymmetric aldol reaction between cyclohexanone and 4-nitrobeznaldehyde. After optimizing the catalytic reaction conditions, we found that the catalyst showed high yield(97%), enantioselectivity(e.e., up to 92%) and anti-diastereoselectivity(up to 95:5) at mild room temperature without any additives.

引用

页码：50 / 54

页数：5

共 50 条

[1] Proline-based Amino Pyridine Dipeptides as Efficient Organocatalysts for Direct Aldol Reaction
GAO Jun-long1
[J]. Chemical Research in Chinese Universities, 2010, 26 (01) : 50 - 54
[2] Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine
Tian, Hua
Gao, Jun-long
Xu, Hao
Zheng, Liang-Yu
Huang, Wen-Bo
Liu, Qing-Wen
Zhang, Suo-Qin
[J]. TETRAHEDRON-ASYMMETRY, 2011, 22 (10) : 1074 - 1080
[3] Proline-Based Polymeric Monoliths: Synthesis, Characterization, and Applications as Organocatalysts in Aldol Reaction
Garg, Dipti
Ahn, J. -H
Chauhan, Ghanshyam S.
[J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2010, 48 (05) : 1007 - 1015
[4] Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review
Shajahan, Rubina
Sarang, Rithwik
Saithalavi, Anas
[J]. CURRENT ORGANOCATALYSIS, 2022, 9 (02) : 124 - 146
[5] Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
Chen, Fubin
Huang, Shi
Zhang, Hui
Liu, Fengying
Peng, Yungui
[J]. TETRAHEDRON, 2008, 64 (40) : 9585 - 9591
[6] Proline-β3-Amino-Ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium
De Nisco, Mauro
Pedatella, Silvana
Ullah, Hidayat
Zaidi, Javid H.
Naviglio, Daniele
Ozdamar, Ozgur
Caputo, Romualdo
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9562 - 9565
[7] Proline-based reduced dipeptides as recyclable and highly enantioselective organocatalysts for asymmetric Michael addition
Cao, Xiaohui
Wang, Ge
Zhang, Richeng
Wei, Yingying
Wang, Wei
Sun, Huichao
Chen, Ligong
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6487 - 6490
[8] Novel chiral proline-based organocatalysts with amide and thiourea-amine units for highly efficient asymmetric aldol reaction in saturated brine without additives
Xu, En-Jie
Song, Yan
Wei, Zhong-Lin
Wang, Rui
Duan, Hai-Feng
Lin, Ying-Jie
Yang, Qing-Biao
Li, Yao-Xian
[J]. CANADIAN JOURNAL OF CHEMISTRY, 2019, 97 (05) : 352 - 359
[9] New and effective proline-based catalysts for asymmetric aldol reaction in water
Yorulmaz, Tugba
Aydogan, Feray
Yolacan, Cigdem
[J]. SYNTHETIC COMMUNICATIONS, 2017, 47 (01) : 78 - 85
[10] Highly efficient prollinamide-based organocatalysts for the direct asymmetric aldol reaction in brine
Jia, Ya-Ning
Wu, Feng-Chun
Ma, Xiao
Zhu, Gong-Jian
Da, Chao-Shan
[J]. TETRAHEDRON LETTERS, 2009, 50 (25) : 3059 - 3062

← 1 2 3 4 5 →