l-Proline supported on ionic liquid-modified magnetic nanoparticles as a highly efficient and reusable organocatalyst for direct asymmetric aldol reaction in water

Literature Information

Publication Date 2013-07-16
DOI 10.1039/C3GC40772A
Impact Factor 10.182
Authors

Yu Kong, Rong Tan, Lili Zhao


View Original

Abstract

Grafting L-proline on imidazolium-based ionic liquid (IL)-functionalized magnetic nanoparticles afforded a magnetically recoverable L-proline catalyst. Characterization technologies suggested the presence of an L-proline backbone, an IL linker, and a magnetic ferrite core in the catalyst. The resulting L-proline catalyst was efficient for direct asymmetric aldol reaction in water without the need for organic solvents and co-catalysts. Such efficiency is attributed to the fact that the IL moiety facilitated the accessibility of hydrophobic reactants to active sites in water and stabilized the formed enamine intermediate during the reaction. High activity (yield = 92%), diastereoselectivity (dr; 88/12) and enantioselectivity (ee; 85%) were obtained using 10 mol% of a catalyst for the reaction between cyclohexanone and 2-nitrobenzaldehyde within 12 h, where the pristine L-proline and IL-free counterpart were almost inactive. The catalyst was easily separated using a permanent magnet externally and can be reused several times without significant loss of activity.

Related Literature

Pentadecaphenylenes: synthesis, self-assembly and complexation with fullerene C60

M. Jalilur Rahman, Hideyuki Shimizu, Masashi Hasegawa, Masahiko Iyoda

2017-04-17 Research Article

DOI: 10.1039/C7QO00258K

Enynone-enabled migratory insertion and Schmittel cyclization cascade for the synthesis of furan-fused fluorenes

He Zhang, Tongxiang Cao, Hejiang Luo, Lianfen Chen, Shifa Zhu

2019-02-21 Research Article

DOI: 10.1039/C9QO00045C

Acid-promoted denitrogenative Pd-catalyzed addition of arylhydrazines with nitriles at room temperature

Kai Cheng, Guofang Wang, Mengting Meng, Chenze Qi

2016-12-13 Research Article

DOI: 10.1039/C6QO00634E

Aqueous MCRs of quaternary ammoniums, N-substituted formamides and sodium disulfide towards aryl thioamides

Zhou Zhou, Jin-Tao Yu, Yongnan Zhou, Yan Jiang, Jiang Cheng

2016-12-19 Research Article

DOI: 10.1039/C6QO00670A

Polymerization of acetylene: polyynes, but not carbyne‡

Dominik Prenzel, Rolf W. Kirschbaum, Wesley A. Chalifoux, Robert McDonald, Michael J. Ferguson, Thomas Drewello

2016-11-08 Research Article

DOI: 10.1039/C6QO00648E

Temperature-controlled helical inversion of asymmetric triphenylamine-based supramolecular polymers; difference of handedness at the micro- and macroscopic levels

Misun Go, Heekyoung Choi, Ka Young Kim, Cheol Joo Moon, Yeonweon Choi, Hiroyuki Miyake, Shim Sung Lee, Sung Ho Jung, Myong Yong Choi, Jong Hwa Jung

2019-02-19 Research Article

DOI: 10.1039/C9QO00051H

Asymmetric hydrogenation of α-hydroxy ketones with an iridium/f-amphox catalyst: efficient access to chiral 1,2-diols

Weilong Wu, Yun Xie, Pan Li, Xiuxiu Li, Yuanhua Liu, Xiu-Qin Dong

2017-01-09 Research Article

DOI: 10.1039/C6QO00810K

Poly[2(6)-aminoazulene]: synthesis, photophysical properties, and proton conductivity

Ian Cheng-Yi Hou, Vijayendra Shetti, Shou-Ling Huang, Kun-Lin Liu, Chi-Yang Chao, Song-Cheng Lin, You-Jen Lin, Li-Yin Chen, Tien-Yau Luh

2017-03-06 Research Article

DOI: 10.1039/C7QO00087A

Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents

Jochen Kirres, Katharina Schmitt, Iris Wurzbach, Frank Giesselmann, Sabine Ludwigs, Mark Ringenberg, Angelika Baro, Sabine Laschat

2017-03-07 Research Article

DOI: 10.1039/C7QO00077D

Fast construction of dianthraceno[a,e]pentalenes for OPV applications

Haijun Fan

2017-01-20 Research Article

DOI: 10.1039/C6QO00867D

You might also like

Compound Q&A

What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?

When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...

40716-16-34-Methyl-6-(trifluor...
Compound Q&A

What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?

4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...

405058-00-64-(3,5-Difluoropheny...
Compound Q&A

How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?

5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...

338982-07-35-{[4-(Trifluorometh...
Compound Q&A

What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?

The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...

6317-57-34-Benzylaniline hydr...
Compound Q&A

Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?

[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...

871329-58-7[3-(Diethylsulfamoyl...
Compound Q&A

What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?

3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...

115929-62-93-Bromo-2,5-dimethox...
Compound Q&A

What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?

N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...

915922-67-7N-Methyl-1-(5-methyl...
Compound Q&A

What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?

This compound is primarily used in the pharmaceutical industry for the synthesis...

24828-96-4Carbamic acid, N-[(5...
Compound Q&A

How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?

2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...

1298101-47-92-Methyl-2-propanyl ...
Compound Q&A

What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?

Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...

367-33-9Ethyl 2-bromo-4,4,4-...

Source Journal

Green Chemistry

Green Chemistry
CiteScore: 16.1
Self-citation Rate: 7.5%
Articles per Year: 944

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.