中文
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (07): 1471-1481 Previous Articles   Next Articles

• Invited Article •

Recent Progress in Self-Supported Chiral Catalysts

Wang Haiming    Wang Zheng    Ding Kuiling**   

  1. (State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China)
  • Received: Online: Published:
  • Contact: Ding Kuiling E-mail:kding@mail.sioc.ac.cn
PDF ( 1715 ) Cited
Export

EndNote

Ris

BibTeX

The immobilization of homogeneous catalysts for recycle and reuse provides an effective way to solve the problems associated with the catalyst cost and metal contamination in a homogeneous catalytic process. Different from the conventional catalyst immobilization methods, the self-supporting strategy utilizes homochiral metal-organic coordination polymers generated by self-assembly of chiral multitopic ligands with metal ions without using any support. The self-supported chiral catalysts as a novel immobilization of homogeneous catalysts strategy demonstrated excellent enantioselectivities in heterogeneous catalysis of a variety of asymmetric reactions. This paper reviews the progress in the research on a variety of heterogeneous asymmetric catalytic reactions with self-supported chiral catalysts.

Contents 
1 Introduction 
2 The concept of the “self-supporting” strategy 
3 Homochiral self-supported catalysts (type Ⅰ) in heterogeneous asymmetric ractions 
3.1 Asymmetric carbon-carbon bond-forming reactions 
3.2 Enantioselective oxidations 
3.3 Enantioselective hydrogenations 
4 Pendant auxiliaries on self-supported catalysts (Type Ⅱ) in heterogeneous asymmetric ractions 
4.1 Asymmetric carbon-carbon bond-forming reactions
4.2 Enantioselective oxidations 
4.3 Enantioselective hydrogenations 
5 Conclusions and outlook

CLC Number: 

[1 ] 杜灿屏(Du C P) ,刘鲁生( Liu L S) ,张恒( Zhang H) . 21 世
纪有机化学发展战略( The Strategies for Developing Organic
Chemistry in 21st Century) . 北京: 化学工业出版社( Beijing:
Chemical Industry Press) ,2002
[2 ] Jacobsen E N, Pfaltz A, Yamamoto H. Comprehensive
Asymmetric Catalysis,Vol. Ⅰ—Ⅲ. Berlin: Springer-Verlag,
1999
[3 ] Noyori R. Asymmetric Catalysis in Organic Synthesis. New
York: Wiley-Interscience,1994
[4 ] Ojima I. Catalytic Asymmetric Synthesis,2nd ed. ,Weinheim:
Wiley-VCH,2000
[5 ] Lin G Q,Li Y M,Chan A S C. Principles and Applications of
Asymmetric Synthesis. Weinheim: Wiley-VCH,2002
[6 ] 李月明( Li Y M) ,范青华( Fan Q H) ,陈新滋( Chan A S C) .
不对称有机反应———催化剂的回收与再利用. 北京: 化学工
业出版社( Beijing: Chemical Industry Press) ,2003
[7 ] Dickerson T J,Reed N N,Janda K D. Chem. Rev. ,2002,
102: 3325—3344
[8 ] Song C E,Lee S G. Chem. Rev. ,2002,102: 3495—3524
[9 ] Heerbeek R V,Kamer P C,Reek J N H. Chem. Rev. ,2002,
102: 3717—3757
[10] Roucoux A, Schulz J, Patin H. Chem. Rev. ,2002,102:
3757—3778
[11] Vankelecom I F J. Chem. Rev. ,2002,102: 3779—3810
[12] McNamara C A,Dixon M J,Bradley M. Chem. Rev. ,2002,
102: 3275—3299
[13] Lu Z L,Lindner E,Mayer H A. Chem. Rev. ,2002,102:
3543—3578
[14] Dupont J,de Souza F R,Suarez P A Z,et al. Chem. Rev. ,
2002,102: 3667—3692
[15] Astruc D,Chardac F. Chem. Rev. ,2001,101: 2991—3023
[16] Clapham B,Reger T S,Janda K D. Tetrahedron,2001,57:
4637—4662
[17] De Vos D E,Vankelecom I F J,Jacobs P A. Chiral Catalyst
Immobilization and Recycling. Weinheim: Wiley-VCH,2000
[18] Fujita M. Molecular Self-Assembly-Organic versus Inorganic
Approaches. Berlin: Springer-Verlag,2000,vol. 96
[19] Fujita M. Chem. Soc. Rev. ,1998,27: 417—425
[20] Yaghi O M,O'Keeffe M,Ockwig N W,et al. Nature,2003,
423: 705—713
[21] Eddaoudi M,Moler D B,Li H L,et al. Acc. Chem. Res. ,
2001,34: 319—330
[22] Lehn J M. Supramolecular Chemistry: Concepts and
Perspectives. Weinheim: Wiley-VCH,1995
[23] Efraty A,Feinstein I. Inorg. Chem. ,1982,21: 3115—3118
[24] Fujita M,Kwon Y J,Washizu S,et al. J. Am. Chem. Soc. ,
1994,116: 1151—1152
[25] Ohmori O,Fujita M. Chem. Commun. ,2004,1586—1587
[26] Kato C N,Ono M,Hino T,et al. Catal. Commun. ,2006,7:
673—677
[27] Kato C N,Mori W. C. R. Chim. ,2007,10: 284—294
[28] Sawaki T,Dewa T,Aoyama Y. J. Am. Chem. Soc. ,1998,
120: 8539—8540
[29] Sawaki T, Aoyama Y. J. Am. Chem. Soc. , 1999, 121:
4793—4798
[30] Perles J,Iglesias M,Monge M A,et al. Chem. Mater. ,2005,
17 : 5837—5842
[31] Henschel A,Gedrich K,Kraehnert R,et al. Chem. Commun. ,
2008,4192—4194
[32] Seo J S,Whang D,Lee H,et al. Nature,2000,404: 982—
986
[33] 石磊( Shi L) ,王正(Wang Z) ,王兴旺(Wang X W) ,李明星
( Li M X) ,丁奎岭(Ding K L) . 有机化学( Chinese Journal of
Organic Chemistry) ,2006,26(10) : 1444—1456
[34] Ding K L,Wang Z,Wang X W,et al. Chem. Eur. J. ,2006,
12: 5188—5197
[35] Ding K L. Pure Appl. Chem. ,2007,79: 1531—1540
[36] Ding K,Wang Z. in Handbook of Asymmetric Heterogeneous
Catalysis ( Eds. Ding K,Uozumi Y) . Weinheim: Wiley-VCH,
2008. 323—355
[37] Wang Z,Chen G,Ding K L. Chem. Rev. ,2009,109: 322—
359
[38] Takizawa S,Somei H,Sasai H,et al. Angew. Chem. Int. Ed. ,
2003,42: 5711—5714
[39] Guo H,Wang X,Ding K L. Tetrahedron Lett. ,2004,45:
2009—2012
[40] Harada T,Nakatsugawa M. Synlett,2006,321—323
[41] Wang X G,Shi L,Ding K L,et al. Angew. Chem. Int. Ed. ,
2005,44: 6362—6366
[42] Wang H,Wang Z,Ding K L. Tetrahedron Lett. ,2009,50:
2200—2203
[43] Wang X S,Wang X W,Ding K L,et al. Chem. Eur. J. ,
2005,11: 4078—4088
[44] van den Berg M,Minnaard A J,Schudde E P,et al. J. Am.
Chem. Soc. ,2000,122: 11539—11540
[45] Pena D,Minnaard A J,de Vries J G,et al. J. Am. Chem.
Soc. ,2002,124: 14552—14553
[46] Wang X W,Ding K L. J. Am. Chem. Soc. ,2004,126:
10524—10525
[47] Shi L,Wang X W,Ding K L,et al. Chem. Eur. J. ,2009,
15: 9855—9867
[48] Shi L,Wang X W,Ding K L,et al. Angew. Chem. Int. Ed. ,
2006,45: 4108—4112
[49] Yu L,Wang Z,Ding K L,et al. Angew. Chem. Int. Ed. ,
2010,49: 3627—3630
[50] Liang Y X,Jing Q,Ding K L,et al. J. Am. Chem. Soc. ,
2005,127: 7694—7695
[51] Wu C D,Hu A,Zhang L,et al. J. Am. Chem. Soc. ,2005,
127: 8940—8941
[52] Wu C D,Lin W. Angew. Chem. Int. Ed. ,2007,46: 1075—
1078
[53] Ngo H L,Hu A,Lin W. J. Mol. Catal. A: Chem. ,2004,
215: 177—186
[54] Cho S H,Ma B,Nguyen S T,et al. Chem. Commun. ,2006,
2563—2565
[55] Cho S H, Gadzikwa T, Afshari M, et al. Eur. J. Inorg.
Chem. ,2007,4863—4867
[56] Hu A,Ngo H L,Lin W. Angew. Chem. Int. Ed. ,2003,42:
6000—6003
[57] Hu A,Ngo H L,Lin W. J. Am. Chem. Soc. ,2003,125:
11490—11491

[1] Ru Jiang, Chenxu Liu, Ping Yang, Shuli You. Condensed Matter Chemistry in Asymmetric Catalysis and Synthesis [J]. Progress in Chemistry, 2022, 34(7): 1537-1547.
[2] Dongxue Han, Xue Jin, Wangen Miao, Tifeng Jiao, Pengfei Duan. Responsiveness of Excited State Chirality Based on Supramolecular Assembly [J]. Progress in Chemistry, 2022, 34(6): 1252-1262.
[3] Bin Li, Ying Yu, Guoxiang Xing, Jinfeng Xing, Wanxing Liu, Tianyong Zhang. Progress in Circularly Polarized Light Emission of Chiral Inorganic Nanomaterials [J]. Progress in Chemistry, 2022, 34(11): 2340-2350.
[4] Minghao Zhou, Shuang Jiang, Tianyong Zhang, Yonghong Shi, Xue Jin, Pengfei Duan. Construction and Optoelectrical Properties of Chiral Perovskite Nanomaterials [J]. Progress in Chemistry, 2020, 32(4): 361-370.
[5] Li Luyao, Xu Xinyao, Zhu Bo, Xu Xinyao. Application of Pyrazolone Compounds in Catalytic Asymmetric Reactions [J]. Progress in Chemistry, 2020, 32(11): 1710-1728.
[6] Jie Yu, Liu-Zhu Gong. Discovery and Typical Advances of Chiral Amino Amide Catalysts [J]. Progress in Chemistry, 2020, 32(11): 1729-1744.
[7] Chenghao Zhu, Junliang Zhang. Palladium Catalyzed Heck-Type Reaction of Organic Halides and Alkyl-Alkynes [J]. Progress in Chemistry, 2020, 32(11): 1745-1752.
[8] Xiangyan Yi, Fei Huang, Jonathan B. Baell, He Huang, Yang Yu. The Formation of C(sp3)-C(sp3) by Visible-Light Photocatalysis [J]. Progress in Chemistry, 2019, 31(4): 505-515.
[9] Yuxia Gao, Yun Liang, Jun Hu, Yong Ju. Supramolecular Chiral Self-Assembly Based on Small Molecular Natural Products [J]. Progress in Chemistry, 2018, 30(6): 737-752.
[10] Yuping Tang, Yanmei He, Yu Feng, Qinghua Fan. Asymmetric Supramolecular Catalysis Based on Macrocyclic Host Molecules [J]. Progress in Chemistry, 2018, 30(5): 476-490.
[11] Yu Zhang, Xiaohua Liu, Lili Lin, Xiaoming Feng*. Recent Advance in Catalytic Asymmetric Friedel-Crafts Reactions [J]. Progress in Chemistry, 2018, 30(5): 491-504.
[12] Zhiyong Han, Liuzhu Gong*. Asymmetric Organo/Palladium Combined Catalysis [J]. Progress in Chemistry, 2018, 30(5): 505-512.
[13] Jun Luo, YanSong Zheng. Chiral Calixarenes and Their Supramolecular Chirality [J]. Progress in Chemistry, 2018, 30(5): 601-615.
[14] Juan Ren, Shen Bian, Yiyun Wang, Xianglei Kong. Magic-Number Cluster of Serine Octamer: Structure and Chiral Characteristics [J]. Progress in Chemistry, 2018, 30(4): 383-397.
[15] Yin Lina, Wang Bin, Ma Ruixue, Yuan Honglin, Yu Gang. Enantioselective Environmental Behavior and Effect of Chiral PPCPs [J]. Progress in Chemistry, 2016, 28(5): 744-753.