Citation: Wenshan Zhao, Chengke Qu, Lili Yang, Yuanchen Cui. Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water[J]. Chinese Journal of Catalysis, ;2015, 36(3): 367-371. doi: 10.1016/S1872-2067(14)60248-5 shu

Chitosan- supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water

1.
a College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, China;

Corresponding author: Yuanchen Cui,
Received Date: 4 September 2014
Available Online: 10 October 2014

Chitosan-supported succinic anhydride-cinchonine (CTS-SA-CN) was synthesized via a two-step route with succinic anhydride as the linker. The catalyst was used to promote the direct asymmetric aldol reaction between cyclohexanone and a variety of aromatic aldehydes in aqueous medium. Aldol adducts were obtained in excellent yields (up to 99%) and good enantioselectivities (up to 96% ee). The CTS-SA-CN catalyst was successfully recycled simply by filtration after use, and was reused 5 times without any significant loss of activity.
- Chitosan,
- Cinchonine,
- Supported catalyst,
- Direct asymmetric aldol reaction
1. [1]
  [1] Machajewski T D, Wong C H, Lerner R A. Angew Chem Int Ed,2000, 39: 1352
2. [2]
  [2] Yoshikawa N, Yamada Y, Das J, Sasai H, Shibasaki M. J Am Chem Soc, 1999, 121: 4168
3. [3]
  [3] Trost B M, Brindle C S. Chem Soc Rev, 2010, 39: 1600
4. [4]
  [4] Markert M, Mulzer M, Schetter B, Mahrwald R. J Am Chem Soc,2007, 129: 7258
5. [5]
  [5] Li H H, He Y H, Yuan Y, Guan Z. Green Chem, 2011, 13: 185
6. [6]
  [6] Zlotin S G, Kucherenko A S, Beletskaya I P. Russ Chem Rev,2009, 78: 737
7. [7]
  [7] Xie B H, Li W, Liu Y, Li H H, Guan Z, He Y H. Tetrahedron,2012, 68: 3160
8. [8]
  [8] Carrea G, Ottolina G, Lazcano A, Pironti V, Colonna S. Tetrahedron: Asymmetry,2007, 18: 1265
9. [9]
  [9] List B, Lerner R A, Barbas C F III. J Am Chem Soc, 2000, 122: 2395
10. [10]
  [10] Hayashi Y, Sumiya T, Takahashi J, Gotoh H, Urushima T, Shoji M. Angew Chem Int Ed, 2006, 45: 958
11. [11]
  [11] Gauchot V, Schmitzer A R. J Org Chem, 2012, 77: 4917
12. [12]
  [12] Gruttadauria M, Giacalone F, Noto R. Chem Soc Rev, 2008, 37: 1666
13. [13]
  [13] Bugde S, Majik M, Mandrekar V, Nadkarni V, Tilve S. Synth Commun,2013, 43: 2536
14. [14]
  [14] Huang W B, Liu Q W, Zheng L Y, Zhang S Q. Catal Lett, 2011, 141: 191
15. [15]
  [15] Pesciaioli F, Righi P, Mazzanti A, Gianelli C, Mancinelli M, Bartoli G, Bencivenni G. Adv Synth Catal, 2011, 353: 2953
16. [16]
  [16] Paradowska J, Rogozińska M, Mlynarski J. Tetrahedron Lett, 2009, 50: 1639
17. [17]
  [17] Zheng B L, Liu Q Z, Guo C S, Wang X L, He L. Org Biomol Chem, 2007, 5: 2913
18. [18]
  [18] Czarnecki P, Plutecka A, Gawroński J, Kacprzak K. Green Chem, 2011, 13: 1280
19. [19]
  [19] Bisai V, Bisai A, Singh V K. Tetrahedron, 2012, 68: 4541
20. [20]
  [20] Cozzi F. Adv Synth Catal, 2006, 348: 1367
21. [21]
  [21] Kristensen T E, Hansen T. Eur J Org Chem,2010: 3179
22. [22]
  [22] Liu Y X, Sun Y N, Tan H H, Liu W, Tao J C. Tetrahedron: Asymmetry, 2007, 18: 2649
23. [23]
  [23] Liu Y X, Sun Y N, Tan H H, Tao J C. Catal Lett, 2008, 120: 281
24. [24]
  [24] Font D, Sayalero S, Bastero A, Jimeno C, Pericàs M A. Org Lett, 2008, 10: 337
25. [25]
  [25] Font D, Jimeno C, Pericás M A. Org Lett, 2006, 8: 4653
26. [26]
  [26] Benaglia M, Celentano G, Cozzi F. Adv Synth Catal, 2001, 343: 171
27. [27]
  [27] Gu L Q, Wu Y Y, Zhang Y Z, Zhao G. J Mol Catal A, 2007, 263: 186
28. [28]
  [28] Dhar D, Beadham I, Chandrasekaran S. Proc Indian Acad Sci Chem Sci, 2003, 115: 365
29. [29]
  [29] Monge-Marcet A, Cattoën X, Alonso D A, Nájera C, Man M W C, Pleixats R. Green Chem, 2012, 14: 1601
30. [30]
  [30] Yan J C, Wang L. Chirality, 2009, 21: 413
31. [31]
  [31] Ni B K, Headley A D. Chem Eur J, 2010, 16: 4426
32. [32]
  [32] Kucherenko A S, Siyutkin D E, Maltsev O V, Kochetkov S V, Zlotin S G. Russ Chem Bull, 2012, 61: 1313
33. [33]
  [33] Qin Y Y, Zhao W S, Yang L L, Zhang X, Cui Y C. Chirality, 2012, 24: 640
34. [34]
  [34] Kumar M N V R. React Funct Polym, 2000, 46: 1
35. [35]
  [35] Cui Y C, Zhang L, Li Y. Polym Advan Technol, 2005, 16: 633
36. [36]
  [36] Vincent T, Guibal E. Ind Eng Chem Res, 2002, 41: 5158
37. [37]
  [37] Viswanathan N, Meenakshi S. J Hazard Mater, 2010, 176: 459
38. [38]
  [38] Reddy K R, Rajgopal K, Maheswari C U, Kantam M L. New J Chem, 2006, 30: 1549
39. [39]
  [39] Ricci A, Bernardi L, Gioia C, Vierucci S, Robitzer M, Quignard F. Chem Commun, 2010, 46: 6288
40. [40]
  [40] Qu C K, Zhao W S, Zhang L, Cui Y C. Chirality, 2014, 26: 209
1. [1]
  Dong-Bing Cheng , Junxin Duan , Haiyu Gao . Experimental Teaching Design on Chitosan Extraction and Preparation of Antibacterial Gel. University Chemistry, 2024, 39(2): 330-339. doi: 10.3866/PKU.DXHX202308053
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [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. [6]
  Haodong JIN , Qingqing LIU , Chaoyang SHI , Danyang WEI , Jie YU , Xuhui XU , Mingli XU . NiCu/ZnO heterostructure photothermal electrocatalyst for efficient hydrogen evolution reaction. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1068-1082. doi: 10.11862/CJIC.20250048
7. [7]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
8. [8]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-0. doi: 10.3866/PKU.WHXB202312024
9. [9]
  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
10. [10]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037
11. [11]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
12. [12]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
13. [13]
  Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti₃C₂T_x MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
14. [14]
  Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112
15. [15]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . Double S-Scheme ZnS/ZnO/CdS Heterostructure Photocatalyst for Efficient Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-0. doi: 10.3866/PKU.WHXB202406020
16. [16]
  Mian Wei , Chang Cheng , Bowen He , Bei Cheng , Kezhen Qi , Chuanbiao Bie . Inorganic-organic CdS/YBTPy S-scheme photocatalyst for efficient hydrogen production and its mechanism. Acta Physico-Chimica Sinica, 2025, 41(12): 100158-0. doi: 10.1016/j.actphy.2025.100158
17. [17]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
18. [18]
  Fangxuan Liu , Ziyan Liu , Guowei Zhou , Tingting Gao , Wenyu Liu , Bin Sun . 中空结构光催化剂. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-0. doi: 10.1016/j.actphy.2025.100071
19. [19]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
20. [20]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434

Get Citation

PDF

XML

Metrics

PDF Downloads(210)
Abstract views(1442)
HTML views(153)

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