ACS Publications. Most Trusted. Most Cited. Most Read
Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2010, 132, 20, 7216-7228
    Article

    Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis
    Click to copy article linkArticle link copied!

    View Author Information
    Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
    [email protected]; [email protected]
    Other Access OptionsSupporting Information (2)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2010, 132, 20, 7216–7228
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja102819g
    Published April 30, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A new approach of asymmetric supramolecular catalysis has been developed by combining the supramolecular recognition of β-cyclodextrin (β-CD) and the superior property of a chiral primary amine catalyst. The resulted β-CD enamine catalysts could effectively promote asymmetric direct aldol reactions with excellent enantioselectivity in an aqueous buffer solution (pH = 4.80). The identified optimal catalyst CD-1 shows interesting characteristics of supramolecular catalysis with selective recognition of aldol acceptors and donors. A detailed mechanistic investigation on such supramolecular catalysis was conducted with the aid of NMR, fluorescence, circular dichroism, and ESI-MS analysis. It is revealed that the reaction is initialized first by binding substrates into the cyclodextrin cavity via a synergistic action of hydrophobic interaction and noncovalent interaction with the CD-1 side chain. A rate-limiting enamine forming step is then involved which is followed by the product-generating C−C bond formation. A subsequent product release from the cavity completes the catalytic cycle. The possible connections between molecular recognition and asymmetric catalysis as well as their relevance to enamine catalysis in both natural enzymes and organocatalysts are discussed based on rational analysis.

    Copyright © 2010 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Detailed experimental procedures and product characterization. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 100 publications.

    1. Xianyin Dai, Lu Tian, Zhixue Liu, Wenshi Xu, Yu-Ping Liu, Yu Liu. Nanoreactor Based on Cyclodextrin for Direct Electrocatalyzed Ammonia Synthesis. ACS Nano 2022, 16 (11) , 18398-18407. https://doi.org/10.1021/acsnano.2c06441
    2. Bingyu Liu, Kaixuan Guo, Naiqi Wang, Aiyou Hao, Pengyao Xing. Manipulating Supramolecular Chirality and Circularly Polarized Luminescence of Cholesteryl Naphthalimides with Multiple Chiral Domains. The Journal of Physical Chemistry C 2022, 126 (30) , 12643-12650. https://doi.org/10.1021/acs.jpcc.2c03340
    3. Alberto Martinez-Cuezva, Adrian Saura-Sanmartin, Mateo Alajarin, Jose Berna. Mechanically Interlocked Catalysts for Asymmetric Synthesis. ACS Catalysis 2020, 10 (14) , 7719-7733. https://doi.org/10.1021/acscatal.0c02032
    4. Niankai Fu, Longji Li, Qi Yang, and Sanzhong Luo . Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones. Organic Letters 2017, 19 (8) , 2122-2125. https://doi.org/10.1021/acs.orglett.7b00746
    5. Qingquan Zhao and Christian E. Schafmeister . Synthesis of Spiroligomer-Containing Macrocycles. The Journal of Organic Chemistry 2015, 80 (18) , 8968-8978. https://doi.org/10.1021/acs.joc.5b01109
    6. Minghua Liu, Li Zhang, and Tianyu Wang . Supramolecular Chirality in Self-Assembled Systems. Chemical Reviews 2015, 115 (15) , 7304-7397. https://doi.org/10.1021/cr500671p
    7. Yuqing Liu, Zhe An, Liwei Zhao, Hui Liu, and Jing He . Enhanced Catalytic Efficiency in the Epoxidation of Alkenes for Manganese Complex Encapsulated in the Hydrophobic Interlayer Region of Layered Double Hydroxides. Industrial & Engineering Chemistry Research 2013, 52 (50) , 17821-17828. https://doi.org/10.1021/ie4026693
    8. Tao Sun, Hui Yan, Guangcun Liu, Jingcheng Hao, Jie Su, Shangyang Li, Pengyao Xing, and Aiyou Hao . Strategy of Directly Employing Paclitaxel To Construct Vesicles. The Journal of Physical Chemistry B 2012, 116 (50) , 14628-14636. https://doi.org/10.1021/jp310261j
    9. Bao-Yu Wang, Teodora Žujović, Daniel A. Turner, Christopher M. Hadad, and Jovica D. Badjić . Design, Preparation, and Study of Catalytic Gated Baskets. The Journal of Organic Chemistry 2012, 77 (6) , 2675-2688. https://doi.org/10.1021/jo202443j
    10. Prabani Dissanayake, Yujiang Mei, and Matthew J. Allen . Luminescence-Decay as an Easy-to-Use Tool for the Study of Lanthanide-Containing Catalysts in Aqueous Solutions. ACS Catalysis 2011, 1 (10) , 1203-1212. https://doi.org/10.1021/cs200213a
    11. Daisuke Shimoyama, Ryo Sekiya, Shoichiro Inoue, Naoyuki Hisano, Shin‐ichi Tate, Takeharu Haino. Conformation Regulation of Trisresorcinarene Directed by Cavity Solvation. Chemistry – A European Journal 2024, 30 (63) https://doi.org/10.1002/chem.202402922
    12. Kentaro Harada, Ryo Sekiya, Takeharu Haino. Kinetic Resolution of Secondary Alcohols Catalyzed at the Exterior of Chiral Coordinated Capsules. Chemistry – A European Journal 2024, 30 (11) https://doi.org/10.1002/chem.202304244
    13. Hongbin Dai, Ran Hong, Yafei Ma, Xiaoxiao Cheng, Wei Zhang. A Subtle Change in the Flexible Achiral Spacer Does Matter in Supramolecular Chirality: Two‐Fold Odd‐Even Effect in Polymer Assemblies. Angewandte Chemie 2023, 135 (50) https://doi.org/10.1002/ange.202314848
    14. Hongbin Dai, Ran Hong, Yafei Ma, Xiaoxiao Cheng, Wei Zhang. A Subtle Change in the Flexible Achiral Spacer Does Matter in Supramolecular Chirality: Two‐Fold Odd‐Even Effect in Polymer Assemblies. Angewandte Chemie International Edition 2023, 62 (50) https://doi.org/10.1002/anie.202314848
    15. Rui Yang, Xiangzhen Meng, Yijia Li, Shanyu Ma, Jiamin Wu, Qing Liu, Shuo Xu, John Tosin Aladejana, Zhen Fang, Changlei Xia, Xianxu Zhan, Jianzhang Li. Durable ultra-high hydrophobic oil absorbing materials based on biomass prepared via a simple low-cost strategy. Journal of Materials Research and Technology 2023, 25 , 725-735. https://doi.org/10.1016/j.jmrt.2023.05.219
    16. Xiao Xiao, Kaini Xu, Zhong-Hua Gao, Zhou-Hao Zhu, Changqing Ye, Baoguo Zhao, Sanzhong Luo, Song Ye, Yong-Gui Zhou, Senmiao Xu, Shou-Fei Zhu, Hongli Bao, Wei Sun, Xiaoming Wang, Kuiling Ding. Biomimetic asymmetric catalysis. Science China Chemistry 2023, 66 (6) , 1553-1633. https://doi.org/10.1007/s11426-023-1578-y
    17. Mao Cai, Runze Zhang, Chunming Yang, Sanzhong Luo. Bio‐inspired Small Molecular Catalysis. Chinese Journal of Chemistry 2023, 41 (5) , 548-559. https://doi.org/10.1002/cjoc.202200628
    18. Yan Liu, Shou‐Heng Liao, Wen‐Tao Dai, Qixia Bai, Shuai Lu, Heng Wang, Xiaopeng Li, Zhe Zhang, Pingshan Wang, Wei Lu, Qi Zhang. Controlled Construction of Heteroleptic [Pd 2 (L A ) 2 (L B )(L C )] 4+ Cages: A Facile Approach for Site‐Selective endo‐Functionalization of Supramolecular Cavities. Angewandte Chemie 2023, 135 (6) https://doi.org/10.1002/ange.202217215
    19. Yan Liu, Shou‐Heng Liao, Wen‐Tao Dai, Qixia Bai, Shuai Lu, Heng Wang, Xiaopeng Li, Zhe Zhang, Pingshan Wang, Wei Lu, Qi Zhang. Controlled Construction of Heteroleptic [Pd 2 (L A ) 2 (L B )(L C )] 4+ Cages: A Facile Approach for Site‐Selective endo‐Functionalization of Supramolecular Cavities. Angewandte Chemie International Edition 2023, 62 (6) https://doi.org/10.1002/anie.202217215
    20. Yingdong Duan, Qifeng Lin, Sanzhong Luo. Asymmetric Electrochemical Organocatalysis: New Opportunities for Synthesis. 2023, 259-270. https://doi.org/10.1002/9783527832217.ch8
    21. Hamzeh Kraus, Niels Hansen. An atomistic view on the uptake of aromatic compounds by cyclodextrin immobilized on mesoporous silica. Adsorption 2022, 28 (3-4) , 125-136. https://doi.org/10.1007/s10450-022-00356-w
    22. Zhuo‐Lin Wang, Yi‐Jun Zhao, Rui Xiong, Li‐Rong Yang, Huan Wang, Jia‐Xing Lu. Electrochemical Asymmetric Reduction of Ketoesters Induced by β‐Cyclodextrin Modified by (1S,2S)‐(+)‐1,2‐Diaminocyclohexane. ChemistrySelect 2021, 6 (4) , 876-879. https://doi.org/10.1002/slct.202004594
    23. Perumal Prabhakaran, Perumal Rajakumar. Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides. RSC Advances 2020, 10 (17) , 10263-10276. https://doi.org/10.1039/C9RA10463A
    24. Qi-Qiang Wang. Supramolecular Catalysis Using Organic Macrocycles. 2020, 829-875. https://doi.org/10.1007/978-981-15-2686-2_36
    25. Michelle P. van der Helm, Benjamin Klemm, Rienk Eelkema. Organocatalysis in aqueous media. Nature Reviews Chemistry 2019, 3 (8) , 491-508. https://doi.org/10.1038/s41570-019-0116-0
    26. Piet W. N. M. van Leeuwen, Matthieu Raynal. Supramolecular Catalysis in Water. 2019, 525-561. https://doi.org/10.1002/9783527814923.ch14
    27. Qi-Qiang Wang. Supramolecular Catalysis Using Organic Macrocycles. 2019, 1-47. https://doi.org/10.1007/978-981-13-1744-6_36-1
    28. Shangyang Li, Xiaoxiao Chu, Aiyou Hao, Ningzhao Shang, Chun Wang. A triply-responsive supramolecular vesicle fabricated by α-cyclodextrin based host–guest recognition and double dynamic covalent bonds. Soft Matter 2018, 14 (48) , 9923-9927. https://doi.org/10.1039/C8SM02113A
    29. . Sanzhong Luo. Angewandte Chemie 2018, 13190-13190. https://doi.org/10.1002/ange.201804818
    30. . Sanzhong Luo. Angewandte Chemie International Edition 2018, 13008-13008. https://doi.org/10.1002/anie.201804818
    31. Guangqing Zhang, Leqin He, Mingxia Yuan, Hui Li, Tao Chang, Shenjun Qin. Clean and Green Procedure for the Synthesis of Biodiesel from the Esterification of Free Fatty Acids and Alcohol Catalyzed by 6-O-(sulfobutyl)-β-cyclodextrin. Russian Journal of Applied Chemistry 2018, 91 (7) , 1123-1128. https://doi.org/10.1134/S1070427218070091
    32. Rui Ning, Yu‐Fei Ao, De‐Xian Wang, Qi‐Qiang Wang. Macrocycle‐Enabled Counteranion Trapping for Improved Catalytic Efficiency. Chemistry – A European Journal 2018, 24 (17) , 4268-4272. https://doi.org/10.1002/chem.201800326
    33. Richard C. Larock, Anton V. Dubrovskiy, Nataliya A. Markina. Formation of Aldehydes and Ketones by Condensation Reactions. 2018, 1-33. https://doi.org/10.1002/9781118662083.cot08-005
    34. Lan Hu, Yan Zhao. Cross‐Linked Micelles with Enzyme‐Like Active Sites for Biomimetic Hydrolysis of Activated Esters. Helvetica Chimica Acta 2017, 100 (8) https://doi.org/10.1002/hlca.201700147
    35. Jian Jiang, Guanghui Ouyang, Li Zhang, Minghua Liu. Self‐Assembled Chiral Nanostructures as Scaffolds for Asymmetric Reactions. Chemistry – A European Journal 2017, 23 (40) , 9439-9450. https://doi.org/10.1002/chem.201700727
    36. Majid M. Heravi, Vahideh Zadsirjan, Mahzad Dehghani, Nastaran Hosseintash. Current applications of organocatalysts in asymmetric aldol reactions: An update. Tetrahedron: Asymmetry 2017, 28 (5) , 587-707. https://doi.org/10.1016/j.tetasy.2017.04.006
    37. Zhang Guangqing, Shenjun Qin, Li Zhen, Han Haiyan, Li Hui, Tao Chang. Coupling reaction of epoxide and carbon dioxide catalysed by alkali metal salts in the presence of ß-cyclodextrin derivatives. World Journal of Engineering 2017, 14 (2) , 159-164. https://doi.org/10.1108/WJE-12-2016-0172
    38. Yafei Guo, Jiuling Li, Xiwei Shi, Yang Liu, Kai Xie, Yuqi Liu, Yubo Jiang, Bo Yang, Rui Yang. Cyclodextrin‐supported palladium complex: A highly active and recoverable catalyst for Suzuki–Miyaura cross‐coupling reaction in aqueous medium. Applied Organometallic Chemistry 2017, 31 (4) https://doi.org/10.1002/aoc.3592
    39. Y. Okamoto, T.R. Ward. Supramolecular Enzyme Mimics. 2017, 459-510. https://doi.org/10.1016/B978-0-12-409547-2.12551-X
    40. Shan-Shan Xue, Meng Zhao, Jing-Xing Lan, Rui-Rong Ye, Yi Li, Liang-Nian Ji, Zong-Wan Mao. Enantioselective hydrolysis of amino acid esters by non-chiral copper complexes equipped with bis (β-cyclodextrin)s. Journal of Molecular Catalysis A: Chemical 2016, 424 , 297-303. https://doi.org/10.1016/j.molcata.2016.09.009
    41. Daniel Fankhauser, Christopher J. Easton. Chirality in Organic Hosts. 2016, 307-342. https://doi.org/10.1002/9781118867334.ch11
    42. Fang Wang, Xian‐Yi Jing, Hang Cong, Zhu Tao. Benzo[3]urils and their Recognition to Metal Cations and Anions. ChemistrySelect 2016, 1 (17) , 5409-5413. https://doi.org/10.1002/slct.201601036
    43. Qingying Zhu, Haimin Shen, Zhujin Yang, Hongbing Ji. Biomimetic asymmetric Michael addition reactions in water catalyzed by amino-containing β-cyclodextrin derivatives. Chinese Journal of Catalysis 2016, 37 (8) , 1227-1234. https://doi.org/10.1016/S1872-2067(15)61122-6
    44. Shan-Shan Xue, Meng Zhao, Zhuo-Feng Ke, Bei-Chen Cheng, Hua Su, Qian Cao, Zhen-Kun Cao, Jun Wang, Liang-Nian Ji, Zong-Wan Mao. Enantioselective Hydrolysis of Amino Acid Esters Promoted by Bis(β-cyclodextrin) Copper Complexes. Scientific Reports 2016, 6 (1) https://doi.org/10.1038/srep22080
    45. Zi-Jian Yao, Shibin Hong, Wei Zhang, Mengyan Liu, Wei Deng. Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium. Tetrahedron Letters 2016, 57 (8) , 910-913. https://doi.org/10.1016/j.tetlet.2016.01.049
    46. Xiao-Jie Song, Zhong-Qiong Qin, Xian-Biao Wang, Fan Yang, Qun-Ling Fang, Chen-Guang She. β-Cyclodextrin Modified With Magnetic Nanoparticles Noncovalently for β-Naphthol Removal From Wastewater. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 2016, 46 (1) , 143-146. https://doi.org/10.1080/15533174.2014.900796
    47. Asha V. Chate, Umesh B. Rathod, Jagdish S. Kshirsagar, Pradip A. Gaikwad, Kishor D. Mane, Pravin S. Mahajan, Mukesh D. Nikam, Charansingh H. Gill. Ultrasound assisted multicomponent reactions: A green method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular reusable catalyst in water. Chinese Journal of Catalysis 2016, 37 (1) , 146-152. https://doi.org/10.1016/S1872-2067(15)61005-1
    48. Yan-Yu Zhu, Mei-Ling Wang, Ming-Xue Ma, Zhen-Gang Sun, Cheng-Qi Jiao, Chao Ma, Huan-Yu Li. Transition metal phosphonates with supramolecular structures: syntheses, structures, surface photovoltage and luminescence properties. New Journal of Chemistry 2016, 40 (1) , 578-588. https://doi.org/10.1039/C5NJ02417J
    49. Aditya N. Khanvilkar, Ashutosh V. Bedekar. Synthesis and characterization of chiral aza-macrocycles and study of their enantiomer recognition ability for organo-phosphoric acid and phosphonic acid derivatives by 31 P NMR and fluorescence spectroscopy. Organic & Biomolecular Chemistry 2016, 14 (9) , 2742-2748. https://doi.org/10.1039/C5OB02616D
    50. Yufeng Ren, Bo Yang, Xiali Liao. Merging supramolecular catalysis and aminocatalysis: amino-appended β-cyclodextrins (ACDs) as efficient and recyclable supramolecular catalysts for the synthesis of tetraketones. RSC Advances 2016, 6 (26) , 22034-22042. https://doi.org/10.1039/C6RA01002D
    51. Tao Sun, Lan Shu, Jian Shen, Chunhui Ruan, Zhifeng Zhao, Chen Jiang. Photo and redox-responsive vesicles assembled from Bola-type superamphiphiles. RSC Advances 2016, 6 (57) , 52189-52200. https://doi.org/10.1039/C6RA05808F
    52. Lifei Zheng, Silvia Sonzini, Masyitha Ambarwati, Edina Rosta, Oren A. Scherman, Andreas Herrmann. Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. Angewandte Chemie 2015, 127 (44) , 13199-13203. https://doi.org/10.1002/ange.201505628
    53. Lifei Zheng, Silvia Sonzini, Masyitha Ambarwati, Edina Rosta, Oren A. Scherman, Andreas Herrmann. Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. Angewandte Chemie International Edition 2015, 54 (44) , 13007-13011. https://doi.org/10.1002/anie.201505628
    54. Saadi Bayat, Abu Bakar Salleh, Emilia Abd Malek, Samira Yousefi, Mohd Basyaruddin Abdul Rahman. Design of a Simple Organocatalysts for Asymmetric Direct Aldol Reactions in Aqueous Medium. Catalysis Letters 2015, 145 (9) , 1750-1755. https://doi.org/10.1007/s10562-015-1583-7
    55. Yingpeng Lu, Gang Zou, Gang Zhao. Primary-secondary diamines catalyzed Michael reaction to generate chiral fluorinated quaternary carbon centers. Tetrahedron 2015, 71 (24) , 4137-4144. https://doi.org/10.1016/j.tet.2015.04.103
    56. Mihály Bartók. Advances in Immobilized Organocatalysts for the Heterogeneous Asymmetric Direct Aldol Reactions. Catalysis Reviews 2015, 57 (2) , 192-255. https://doi.org/10.1080/01614940.2015.1039432
    57. Haydee Rojas Cabrera, Gabriela Huelgas, Julio M. Hernández Pérez, Patrick J. Walsh, Ratnasamy Somanathan, Cecilia Anaya de Parrodi. Homochiral l-prolinamido-sulfonamides and their use as organocatalysts in aldol reactions. Tetrahedron: Asymmetry 2015, 26 (4) , 163-172. https://doi.org/10.1016/j.tetasy.2015.01.009
    58. P. Ballester, PWNM van Leeuwer, A Vidal-Ferran. Supramolecular Catalysis. 2015https://doi.org/10.1016/B978-0-12-409547-2.11500-8
    59. Kegang Liu, Guoqi Zhang. Direct asymmetric aldol reactions in aqueous media catalyzed by a β-cyclodextrin–proline conjugate with a urea linker. Tetrahedron Letters 2015, 56 (1) , 243-246. https://doi.org/10.1016/j.tetlet.2014.11.084
    60. Huanqing Chen, Jiazeng Fan, Xiaoshi Hu, Junwei Ma, Shilu Wang, Jian Li, Yihua Yu, Xueshun Jia, Chunju Li. Biphen[n]arenes. Chemical Science 2015, 6 (1) , 197-202. https://doi.org/10.1039/C4SC02422B
    61. Hugo Fanlo‐Virgós, Andrea‐Nekane R. Alba, Saleh Hamieh, Mathieu Colomb‐Delsuc, Sijbren Otto. Transient Substrate‐Induced Catalyst Formation in a Dynamic Molecular Network. Angewandte Chemie 2014, 126 (42) , 11528-11532. https://doi.org/10.1002/ange.201403480
    62. Hugo Fanlo‐Virgós, Andrea‐Nekane R. Alba, Saleh Hamieh, Mathieu Colomb‐Delsuc, Sijbren Otto. Transient Substrate‐Induced Catalyst Formation in a Dynamic Molecular Network. Angewandte Chemie International Edition 2014, 53 (42) , 11346-11350. https://doi.org/10.1002/anie.201403480
    63. Zhong Luo, Yan Hu, Kaiyong Cai, Xingwei Ding, Quan Zhang, Menghuan Li, Xing Ma, Beilu Zhang, Yongfei Zeng, Peizhou Li, Jinghua Li, Junjie Liu, Yanli Zhao. Intracellular redox-activated anticancer drug delivery by functionalized hollow mesoporous silica nanoreservoirs with tumor specificity. Biomaterials 2014, 35 (27) , 7951-7962. https://doi.org/10.1016/j.biomaterials.2014.05.058
    64. Niejun Wang, Lilin Zhou, Jun Guo, Qiquan Ye, Jin-Ming Lin, Jinying Yuan. Adsorption of environmental pollutants using magnetic hybrid nanoparticles modified with β-cyclodextrin. Applied Surface Science 2014, 305 , 267-273. https://doi.org/10.1016/j.apsusc.2014.03.054
    65. Shangyang Li, Pengyao Xing, Lin Zhang, Feifei Xin, Jinhui Nie, Hailu Wang, Mingfang Ma, Yurong Wu, Aiyou Hao. Controllable self-assembly of an amphiphilic drug with β-cyclodextrin and α-amylase. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2014, 445 , 67-74. https://doi.org/10.1016/j.colsurfa.2014.01.020
    66. Qian Zhang, Yong-Zhen Huang, Jun-Hui Yang, Bai-Wei Ma, Gui-Rong Qu, Hai-Ming Guo. Synthesis of 9-oxiranyl-9H-purine derivatives in β-cyclodextrin cavity. Tetrahedron Letters 2014, 55 (6) , 1203-1206. https://doi.org/10.1016/j.tetlet.2013.12.117
    67. Evgeny A. Kataev, Christoph Müller. Recent advances in molecular recognition in water: artificial receptors and supramolecular catalysis. Tetrahedron 2014, 70 (2) , 137-167. https://doi.org/10.1016/j.tet.2013.11.010
    68. Matthieu Raynal, Pablo Ballester, Anton Vidal-Ferran, Piet W. N. M. van Leeuwen. Supramolecular catalysis. Part 2: artificial enzyme mimics. Chem. Soc. Rev. 2014, 43 (5) , 1734-1787. https://doi.org/10.1039/C3CS60037H
    69. Niankai Fu, Long Zhang, Sanzhong Luo, Jin‐Pei Cheng. Chiral Primary‐Amine‐Catalyzed Conjugate Addition to α‐Substituted Vinyl Ketones/Aldehydes: Divergent Stereocontrol Modes on Enamine Protonation. Chemistry – A European Journal 2013, 19 (46) , 15669-15681. https://doi.org/10.1002/chem.201302056
    70. Haruyasu Asahara, Toshiyuki Kida, Tomoaki Hinoue, Mitsuru Akashi. Cyclodextrin host as a supramolecular catalyst in nonpolar solvents: stereoselective synthesis of (E)-3-alkylideneoxindoles. Tetrahedron 2013, 69 (45) , 9428-9433. https://doi.org/10.1016/j.tet.2013.08.078
    71. Fei Ye, Zhan‐Jiang Zheng, Wen‐Hui Deng, Long‐Sheng Zheng, Yuan Deng, Chun‐Gu Xia, Li‐Wen Xu. Modulation of Multifunctional N,O,P Ligands for Enantioselective Copper‐Catalyzed Conjugate Addition of Diethylzinc and Trapping of the Zinc Enolate. Chemistry – An Asian Journal 2013, 8 (9) , 2242-2253. https://doi.org/10.1002/asia.201300544
    72. Jing-Ru Song, Zhi-Tang Huang, Qi-Yu Zheng. Synthesis of functionalized cyclotriveratrylene analogues with C1-symmetry and the application for 1,4-Michael addition of alcohols to unsaturated aryl ketone. Tetrahedron 2013, 69 (35) , 7308-7313. https://doi.org/10.1016/j.tet.2013.06.077
    73. Yan-Jun Lin, Bo-Kai Tsai, Chia-Jung Tu, Jingyueh Jeng, Chih-Chien Chu. Synthesis of β-cyclodextrin and poly(amido amine) dendron click cluster and its synergistic binding property. Tetrahedron 2013, 69 (7) , 1801-1807. https://doi.org/10.1016/j.tet.2012.12.073
    74. Haruyasu Asahara, Takuya Iwamoto, Toshiyuki Kida, Mitsuru Akashi. Unique catalytic effect of a cyclodextrin host on photodimerization of coumarin in nonpolar solvents. Tetrahedron Letters 2013, 54 (7) , 688-691. https://doi.org/10.1016/j.tetlet.2012.12.006
    75. P. Ballester, P.W.N.M. van Leeuwen, A. Vidal. Supramolecular Catalysis. 2013, 457-486. https://doi.org/10.1016/B978-0-08-097774-4.00617-3
    76. Joshua Schmidt, Clayton Ehasz, Michael Epperson, Kimberly Klas, Justin Wyatt, Mirko Hennig, Marcello Forconi. The effect of the hydrophobic environment on the retro-aldol reaction: comparison to a computationally-designed enzyme. Organic & Biomolecular Chemistry 2013, 11 (48) , 8419. https://doi.org/10.1039/c3ob41898g
    77. Cyprian M. M’thiruaine, Holger B. Friedrich, Evans O. Changamu, Bernard Omondi. Regioselective reactions of electrophilic iron dicarbonyl cations, [(η5-C5R5)(CO)2Fe]+ (R = H, CH3) with heterofunctional amine ligands. Journal of Organometallic Chemistry 2012, 717 , 52-60. https://doi.org/10.1016/j.jorganchem.2012.06.034
    78. Qian Zhang, Gang Cheng, Yong-Zhen Huang, Gui-Rong Qu, Hong-Ying Niu, Hai-Ming Guo. Regioselective N9 alkylation of purine rings assisted by β-cyclodextrin. Tetrahedron 2012, 68 (38) , 7822-7826. https://doi.org/10.1016/j.tet.2012.07.025
    79. Motomu Kanai, Takao Ikariya, Takashi Ooi, Kuiling Ding, David Milstein. Recent Topics in Cooperative Catalysis: Asymmetric Catalysis, Polymerization, Hydrogen Activation, and Water Splitting. 2012, 385-412. https://doi.org/10.1002/9783527664801.ch11
    80. Hai-Min Shen, Hong-Bing Ji. Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water. Tetrahedron Letters 2012, 53 (28) , 3541-3545. https://doi.org/10.1016/j.tetlet.2012.04.140
    81. Hai-Min Shen, Hong-Bing Ji. Amino alcohol-modified β-cyclodextrin inducing biomimetic asymmetric oxidation of thioanisole in water. Carbohydrate Research 2012, 354 , 49-58. https://doi.org/10.1016/j.carres.2012.03.034
    82. Vishnumaya Bisai, Alakesh Bisai, Vinod K. Singh. Enantioselective organocatalytic aldol reaction using small organic molecules. Tetrahedron 2012, 68 (24) , 4541-4580. https://doi.org/10.1016/j.tet.2012.03.099
    83. Michelangelo Gruttadauria, Lucia Anna Bivona, Paolo Lo Meo, Serena Riela, Renato Noto. Sequential Suzuki/Asymmetric Aldol and Suzuki/Knoevenagel Reactions Under Aqueous Conditions. European Journal of Organic Chemistry 2012, 2012 (13) , 2635-2642. https://doi.org/10.1002/ejoc.201200092
    84. Wei Zhao, Qin Zhong. Recent advance of cyclodextrins as nanoreactors in various organic reactions: a brief overview. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2012, 72 (1-2) , 1-14. https://doi.org/10.1007/s10847-011-9983-9
    85. Jesús García, Lucas G. Martins, Miquel Pons. NMR Spectroscopy in Solution. 2012https://doi.org/10.1002/9780470661345.smc019
    86. Stephen F. Lincoln, Duc‐Truc Pham. Cyclodextrins: From Nature to Nanotechnology. 2012https://doi.org/10.1002/9780470661345.smc055
    87. Ai‐Bao Xia, Dan‐Qian Xu, Chao Wu, Long Zhao, Zhen‐Yuan Xu. Organocatalytic Diels–Alder Reactions Catalysed by Supramolecular Self‐Assemblies Formed from Chiral Amines and Poly(alkene glycol)s. Chemistry – A European Journal 2012, 18 (4) , 1055-1059. https://doi.org/10.1002/chem.201102766
    88. Zhiyun Du, Bo Qin, Chang Sun, Ying Liu, Xi Zheng, Kun Zhang, Allan H. Conney, Huaqiang Zeng. Folding-promoted TBAX-mediated selective demethylation of methoxybenzene-based macrocyclic aromatic pentamers. Organic & Biomolecular Chemistry 2012, 10 (21) , 4164. https://doi.org/10.1039/c2ob25160d
    89. Yaomei Jia, Zhifeng Mao, Rui Wang. Asymmetric triple cascade organocatalytic reaction in water: construction of polyfunctional cyclohexene building blocks having multiple stereocenters. Tetrahedron: Asymmetry 2011, 22 (23) , 2018-2023. https://doi.org/10.1016/j.tetasy.2011.11.023
    90. Niankai Fu, Long Zhang, Jiuyuan Li, Sanzhong Luo, Jin‐Pei Cheng. Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate. Angewandte Chemie 2011, 123 (48) , 11653-11657. https://doi.org/10.1002/ange.201105477
    91. Niankai Fu, Long Zhang, Jiuyuan Li, Sanzhong Luo, Jin‐Pei Cheng. Chiral Primary Amine Catalyzed Enantioselective Protonation via an Enamine Intermediate. Angewandte Chemie International Edition 2011, 50 (48) , 11451-11455. https://doi.org/10.1002/anie.201105477
    92. Yingpeng Lu, Changwu Zheng, Yingquan Yang, Gang Zhao, Gang Zou. Highly Enantioselective Epoxidation of α,β‐Unsaturated Ketones Catalyzed by Primary‐Secondary Diamines. Advanced Synthesis & Catalysis 2011, 353 (17) , 3129-3133. https://doi.org/10.1002/adsc.201100230
    93. Ya-Jie An, Chuan-Chuan Wang, Yuan-Zhen Xu, Wei-Juan Wang, Jing-Chao Tao. Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media. Catalysis Letters 2011, 141 (8) , 1123-1129. https://doi.org/10.1007/s10562-011-0574-6
    94. Shenshen Hu, Long Zhang, Jiuyuan Li, Sanzhong Luo, Jin‐Pei Cheng. Chiral Primary Amine Catalyzed Asymmetric Direct Cross‐Aldol Reaction of Acetaldehyde. European Journal of Organic Chemistry 2011, 2011 (18) , 3347-3352. https://doi.org/10.1002/ejoc.201100267
    95. Wangsheng Sun, Liang Hong, Rui Wang. Facile Creation of 2‐Substituted Indolin‐3‐ones by Using Primary–Secondary Diamine Catalysts. Chemistry – A European Journal 2011, 17 (22) , 6030-6033. https://doi.org/10.1002/chem.201100144
    96. Yan Kang, Lilin Zhou, Xia Li, Jinying Yuan. β-Cyclodextrin-modified hybrid magnetic nanoparticles for catalysis and adsorption. Journal of Materials Chemistry 2011, 21 (11) , 3704. https://doi.org/10.1039/c0jm03513k
    97. Long Zhang, Sanzhong Luo, Jin-Pei Cheng. Non-covalent immobilization of asymmetric organocatalysts. Catalysis Science & Technology 2011, 1 (4) , 507. https://doi.org/10.1039/c1cy00029b
    98. Jian Wang, Chengyong Liu, Dongdong Ding, Lixi Zeng, Qian Cao, Hui Zhang, Hong Zhao, Xiangjun Li, Kaixiang Xiang, Yujian He, Guangwei Wang. Aggregation of an anionic porphyrin with chiral metal complexes and the competitive binding influences of a surfactant and a polyelectrolyte. New Journal of Chemistry 2011, 35 (7) , 1424. https://doi.org/10.1039/c1nj20193j
    99. Salvador Tomas. Bioinspired organic chemistry. Annual Reports Section "B" (Organic Chemistry) 2011, 107 , 390. https://doi.org/10.1039/c1oc90018h
    100. Anneleen L. W. Demuynck, Jozef Vanderleyden, Bert F. Sels. Direct Asymmetric syn ‐Aldol Reactions of Linear Aliphatic Ketones with Primary Amino Acid‐Derived Diamines. Advanced Synthesis & Catalysis 2010, 352 (14-15) , 2421-2426. https://doi.org/10.1002/adsc.201000419
    Download PDF
    Go to Journal of the American Chemical Society
    Get e-Alerts
    Get e-Alerts

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2010, 132, 20, 7216–7228
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja102819g
    Published April 30, 2010
    Copyright © 2010 American Chemical Society
    Request reuse permissions

    Article Views

    8909

    Altmetric

    -

    Citations

    100
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.