Citation: Jianwei Wei, Wengang Guo, Boyu Zhang, Yan Liu, Xin Du, Can Li. An amphiphilic organic catalyst for the direct asymmetric Michael addition of cycloketone to nitroolefins in water[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1008-1011. doi: 10.1016/S1872-2067(14)60080-2 shu

An amphiphilic organic catalyst for the direct asymmetric Michael addition of cycloketone to nitroolefins in water

Jianwei Wei ^a,b ,
Wengang Guo ^b ,
Boyu Zhang ^b ,
Yan Liu ^b,, ,
Xin Du ^a,, ,
Can Li ^b,,

1.
a. Department of Chemistry, Dalian University of Technology, Dalian 116024, Liaoning, China;

Corresponding author: Yan Liu, Xin Du, Can Li,
Received Date: 21 December 2013
Available Online: 11 March 2014
Fund Project:

A series of amphiphilic proline-derived mercapto imidazole organic catalysts were synthesized and shown to be very effective with an acid cocatalyst for the asymmetric Michael addition reaction of ketones to nitroolefins with high diastereoselectivity (up to 99:1) and execellent enantioselectivity (up to 96%) using water as solvent.
- Asymmetric catalysis,
- Emulsion,
- Organocatalysis,
- Michael addition
1. [1]
  [1] Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. Pergamon: Oxford, 1992
2. [2]
  [2] List B, Pojarliev P, Martin H J. Org Lett, 2001, 3: 2423
3. [3]
  [3] Alexakis A, Andrey O. Org Lett, 2002, 4: 3611
4. [4]
  [4] Luo S Z, Xu H, Mi X, Li J, Zheng X, Cheng J P. J Org Chem, 2006, 71: 9244
5. [5]
  [5] Mo L, Tang H, Yao Z. Tetrahedron, 2013, 33: 6897
6. [6]
  [6] Zhao H, Li H, Yue Y, Sheng Z. Eur J Org Chem, 2013, 2013: 1740
7. [7]
  [7] Zhong J, Guan Z, He Y. Catal Commun, 2013, 32: 18
8. [8]
  [8] Lu A, Gao P, Wu Y, Wang Y, Zhou Z, Tang C. Org Biomo Chem, 2009, 7: 3141
9. [9]
  [9] Czekelius C, Carreira E M. Angew Chem Int Ed, 2005, 44: 612
10. [10]
  [10] Mase N, Watanabe K, Yoda H, Takabe K, Tanaka F, Barbas III C F. J Am Chem Soc, 2006, 128: 4966
11. [11]
  [11] Luo S Z, Mi X, Liu S, Cheng J P. Chem Commun, 2006, 35: 3687
12. [12]
  [12] Syu S, Kao T, Lin W. Tetrahedron, 2010, 66: 891
13. [13]
  [13] Wang J J, Lao J H, Du D S, Nie S Z, Hu Z P, Yan M. Chirality, 2012, 24: 232
14. [14]
  [14] Chuan Y M, Chen G H, Peng Y G. Tetrahedron Lett, 2009, 50: 3054
15. [15]
  [15] Ibrahem I, Cordova A. Tetrahedron Lett, 2005, 46: 3363
16. [16]
  [16] Zhong L, Gao Q, Gao J, Xiao J, Li C. J Catal, 2007, 250: 360
17. [17]
  [17] Mase N, Noshiro N, Mokuya A, Takabe K. Adv Synth Catal, 2009, 351: 2791
18. [18]
  [18] Gao Q, Liu Y, Lu S M, Li J, Li C. Green Chem, 2011, 13: 1983
19. [19]
  [19] Zhang B Y, Jiang Z X, Zhou X, Lu S M, Li J, Liu Y, Li C. Angew Chem Int Ed, 2012, 51: 13159
1. [1]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
2. [2]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
3. [3]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
4. [4]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
5. [5]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
6. [6]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
7. [7]
  Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
8. [8]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
9. [9]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
10. [10]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-0. doi: 10.3866/PKU.WHXB202312014
11. [11]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
12. [12]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
13. [13]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
14. [14]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
15. [15]
  Jingping Li , Suding Yan , Jiaxi Wu , Qiang Cheng , Kai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO₄. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104
16. [16]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
17. [17]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
18. [18]
  Shuang Cao , Bo Zhong , Chuanbiao Bie , Bei Cheng , Feiyan Xu . Insights into Photocatalytic Mechanism of H₂ Production Integrated with Organic Transformation over WO₃/Zn_0.5Cd_0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016
19. [19]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . Architecting Inorganic/Organic S-Scheme Heterojunction of Bi₄Ti₃O₁₂ Coupling with g-C₃N₄ for Photocatalytic H₂O₂ Production from Pure Water. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-0. doi: 10.3866/PKU.WHXB202403009
20. [20]
  Yuanqing Wang , Yusong Pan , Hongwu Zhu , Yanlei Xiang , Rong Han , Run Huang , Chao Du , Chengling Pan . Enhanced Catalytic Activity of Bi₂WO₆ for Organic Pollutants Degradation under the Synergism between Advanced Oxidative Processes and Visible Light Irradiation. Acta Physico-Chimica Sinica, 2024, 40(4): 2304050-0. doi: 10.3866/PKU.WHXB202304050

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(747)
HTML views(63)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142