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
-
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.
-
Keywords:
- Asymmetric catalysis,
- Emulsion,
- Organocatalysis,
- Michael addition
-
-
-
[1]
[1] Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. Pergamon: Oxford, 1992
-
[2]
[2] List B, Pojarliev P, Martin H J. Org Lett, 2001, 3: 2423
-
[3]
[3] Alexakis A, Andrey O. Org Lett, 2002, 4: 3611
-
[4]
[4] Luo S Z, Xu H, Mi X, Li J, Zheng X, Cheng J P. J Org Chem, 2006, 71: 9244
-
[5]
[5] Mo L, Tang H, Yao Z. Tetrahedron, 2013, 33: 6897
-
[6]
[6] Zhao H, Li H, Yue Y, Sheng Z. Eur J Org Chem, 2013, 2013: 1740
-
[7]
[7] Zhong J, Guan Z, He Y. Catal Commun, 2013, 32: 18
-
[8]
[8] Lu A, Gao P, Wu Y, Wang Y, Zhou Z, Tang C. Org Biomo Chem, 2009, 7: 3141
-
[9]
[9] Czekelius C, Carreira E M. Angew Chem Int Ed, 2005, 44: 612
-
[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] Luo S Z, Mi X, Liu S, Cheng J P. Chem Commun, 2006, 35: 3687
-
[12]
[12] Syu S, Kao T, Lin W. Tetrahedron, 2010, 66: 891
-
[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] Chuan Y M, Chen G H, Peng Y G. Tetrahedron Lett, 2009, 50: 3054
-
[15]
[15] Ibrahem I, Cordova A. Tetrahedron Lett, 2005, 46: 3363
-
[16]
[16] Zhong L, Gao Q, Gao J, Xiao J, Li C. J Catal, 2007, 250: 360
-
[17]
[17] Mase N, Noshiro N, Mokuya A, Takabe K. Adv Synth Catal, 2009, 351: 2791
-
[18]
[18] Gao Q, Liu Y, Lu S M, Li J, Li C. Green Chem, 2011, 13: 1983
-
[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]
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]
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
-
[4]
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
-
[5]
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
-
[6]
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
-
[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]
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-. doi: 10.3866/PKU.WHXB202312014
-
[9]
.
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): -. -
[10]
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
-
[11]
Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
-
[12]
Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
-
[13]
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
-
[14]
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
-
[15]
Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
-
[16]
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
-
[17]
Haiyu Nie , Chenhui Zhang , Fengpei Du . Ideological and Political Design for the Preparation, Characterization and Particle Size Control Experiment of Nanoemulsion. University Chemistry, 2024, 39(2): 41-46. doi: 10.3866/PKU.DXHX202306055
-
[18]
Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
-
[19]
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
-
[20]
Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(641)
- HTML views(58)