中文
Earlier issues
Announcement
More
Progress in Chemistry 2000, Vol. 12 Issue (03): 305- Previous Articles   Next Articles

• Review •

Synthesis of Chiral Phosphine Ligands and Their Applications in Asymmetric Catalysis

Li Yanyun;Xia Chungu**;Xie Baohan   

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
  • Received: Revised: Online: Published:
  • Contact: Xia Chungu
PDF ( 2878 ) Cited
Export

EndNote

Ris

BibTeX

The progress in synthesis of chiral phosphine ligands is reviewed. Their applications in asymmetric hydrogenation, asymmetric hydroformylation and asymmetric hydroesterification are described.
Key words: chiral phosphine ligands, asymmetric catalysis

CLC Number: 

[1 ] Chem. Eng. News, 1989, 16, 50.
[2 ] 赵培庆(Zhao P Q ) , 宫照阳(Gong Z Y) , 分子催化(J. Mol. Catal. ) , 1997, 11 (6) , 427.
[3 ] Dentsch D H, Chem. Tech. , 1991, 3, 157.
[4 ] Kagan H B, in Comprehension Organometallic Chemistry , Pergamon Press, Oxford, 1985, 8, 463.
[5 ] Blystone S L , Chem. Rev. , 1989, 89, 1663.
[6 ] Meyers A I, Tetrahedron, 1992, 48, 2589.
[7 ] Wenzel T F, Morin C A , Brechting A A , J. Org. Chem. , 1992, 57, 3594.
[8 ] Prikle W H, Welch C T , Lamm B, J. Org. Chem. , 1992, 57, 3854.
[9 ] Consiglio G, Catalytic Asymmetric Synthesis (ed. Ojima I) , VCH Publisher, New York, 1993, 273.
[10 ] Noyori R, Asymmetric Catalysisin Organic Synthesis, John Wiley & Sons, New York, 1994.
[11 ] 日本化学会编, 张正义译, 有机金属络合物化学, 化学工业出版社, 1990, 第10 章, 305—339.
[12 ] Knowles W S, J. Chem. Edu. , 1986, 63, 222.
[13 ] 显谷忠俊Aratani T , 化学增刊(Kagaku Zokan) , 1985, 105, 133.
[14 ] Tani K, Yamagata T , Akutagawa S et al. , J. Am. Chem. Soc. , 1984, 106, 5208.
[15 ] Parpall G W , Nugent W A , Chem. Tech. , 1988, 18 (6) , 380.
[16 ] Chirality in Industry (eds. Collins A N , Sheldrake G N , Crosby J ) , John Wiley & Sons, New York,1992.
[17 ] Applied Homogeneous Catalysis with Organometallic Compounds (eds. Cornils B, Herrmann W A ) ,VCH, Weinheim 1996, 29.
[18 ] 宓爱巧(Mi A Q ) , 孙健(Sun J ) , 陈新滋(Chen X Z) 等, 合成化学(Chinese Journal of Synthetic Chemistry ) , 1995, 3 (1) , 19.
[19 ] 吕士杰(Lü S J ) , 王来来(Wang L L ) , 分子催化(Journal of Molecular Catalysis) , 1997, 11 (6) ,476.
[20 ] Kagan H B, Adv. Catal. , 1986, 25, 88.
[21 ] Pietrusiewicz K M , Zablocka M , Chem. Rev. , 1994, 94, 1375.
[22 ] Imamoto T , In Handbook of Organophosphorus Chemistry (ed. Engel R ) , Marcel Dekker, New York, 1992, Chapter 1.
[23 ] Kagan H B, Sasaki M , In Chemistry of Organophosphorus Compounds (ed. Hartley F R) , John Wiley & Sons, New York 1990, Vol. 1, Chapter 3.
[24 ] Valentine D J r, In Asymmetric Synthesis, (eds. Morrison J D, Scott J W ) , Academic Press, New York , 1984, , Vol. 4, Chapter 3.
[25 ] Burgess K, Ohlmeyer M J , Whitmire K H, Organometallics, 1992, 11, 3588.
[26 ] Corey E J , Chen Z, Tanoury G J , J. Am. Chem. Soc. , 1993, 115, 11000.
[27 ] Nagel V , Krink T, Angew. Chem. Int. Ed. Engl. , 1993, 32, 1052.
[28 ] Imamoto T , Tsuruta H, Wada Yet al. , Tetrahedron Lett. , 1995, 36, 8271.
[29 ] Brenchley G, Fedouloff M , Mahon M F et al. , Tetrahedron, 1995, 51, 10581.
[30 ] Brenchley G, Fedouloff M , Merifield E et al. , Tetrahedron: Asymmetry , 1996, 7, 2809.
[31 ] Vedejs E, Donde Y, J. Am. Chem. Soc. , 1997, 119, 9293.
[32 ] Aw B H, Andy Hor T S, Selvaratnam S et al. , Inorg. Chem. , 1997, 36, 2138.
[33 ] Imamoto T , Watanabe J , Wada Y et al. , J. Am. Chem. Soc. , 1998, 120 , 1635.
[34 ] Uozumi Y, Hayashi T , J. Am. Chem. Soc. , 1991, 113, 9887.
[35 ] Uozumi Y, Tanahashi A , Lee S Y, J. Org. Chem. , 1993, 58, 1945.
[36 ] Hayashi T , Iwamura H, Naito M et al. , J. Am. Chem. Soc. , 1994, 116, 775.
[37 ] Brenchley G, Merifield E, Wills M et al. , Tetrahedron Lett. , 1994, 35, 2791.
[38 ] Uozumi Y, Suzuki N , Ogiwara A et al. , Tetrahedron, 1994, 50, 4293.
[39 ] Marinetti A , Tetrahedron Lett. , 1994, 35, 5861.
[40 ] Marinetti A , Richard L , Organometallics, 1994, 13, 3956.
[41 ] Uozumi Y, Kitayama K, Hayashi T, J. Chem. Soc. , Chem. Commun. , 1995, 1533.
[42 ] Kitayama K, Tsuji H, Uozumi Y et al. , Tetrahedron Lett. , 1996, 37, 4169.
[43 ] Hamada Y, Seto N , Ohmori H et al. , Tetrahedron Lett. , 1996, 37, 7565.
[44 ] Chen Z G, Jiang Q Z, Zhu G X et al. , J. Org. Chem. , 1997, 62, 4521.
[45 ] Zhu G X, Chen Z G, Jiang Q Z et al. , J. Am. Chem. Soc. , 1997, 119, 3836.
[46 ] Meek D W , In Homogeneous Catalysis with Metal Phosphine Complexes (ed. Pignolet L ) , New York, Plenum Press, 1983, Chap ter 8.
[47 ] Fryzuk M D, Bosnich B, J. Am. Chem. Soc. , 1977, 99, 6262.
[48 ] Mcneil P A , Roberts N K, Bonisch B, J. Am. Chem. Soc. , 1981, 103, 2280.
[49 ] Miyashita A , Yasuda A , Takaya H et al. , J. Am. Chem. S oc. , 1980, 102, 7932.
[50 ] Miyashita A , Takaya H, Souchi T et al. , Tetrahedron, 1984, 40, 1245.
[51 ] Takaya H, Mashima K, Koyano K et al. , J. Org. Chem. , 1986, 51, 629.
[52 ] Takaya H, Akutagawa S, Noyori R, Org. Synth. , 1988, 67, 20.
[53 ] Burk M J , Feaster J E, Harlow R L , Organometallics, 1990, 9, 2653.
[54 ] Burk M J , J. Am. Chem. Soc. , 1991, 113, 8518.
[55 ] Burk M J , Feaster J E, Nugent W A et al. , J. Am. Chem. Soc. , 1993, 15, 10125.
[56 ] Burk M J , Lee J R, Martinez J P, J. Am. Chem. Soc. , 1994, 116, 10847.
[57 ] Zhu G X, Cao P, Jiang Q Z et al. , J. Am. Chem. Soc. , 1997, 119, 1799.
[58 ] Babin J , W O 93/03839, 1993 (Chem. Abstr. , 1993, 119, 159872).
[59 ] Sakai N , Mano S, Nozaki K et al. , J. Am. Chem. Soc. , 1993, 115, 7033.
[60 ] 牟宗刚(Mou Z G) , 吕士杰(Lü S J ) , 周宏英(Zhou H Y) 等, 分子催化(Journal of Molecular Catalysis ) , 1996, 10 (2) , 149.
[61 ] Hayashi T , Ohnol A , Lu S J et al. , J. Am. Chem. Soc. , 1994, 116, 4221.
[62 ] Ojima I, Yoda N , Tetrahedron Lett. , 1980, 21, 1051.
[63 ] Ojima I, Pure and Appl. Chem. , 1984, 56, 99.
[64 ] Karim A , Mortreux A , Petit F, J. Organomet. Chem. , 1986, 312, 375.
[65 ] Benincori T , Brenna E, Sannicolo F et al. J. Org. Chem. , 1996, 61, 6244.
[66 ] Jiang Y T , Jiang Q Z, Zhu G X et al. , Tetrahed ron Lett. , 1997, 38, 215.
[67 ] Zhang F Y, Pai C C et al. , J. Am. Chem. Soc. , 1998, 120, 5808.
[68 ] Mi A Q , Lou R L , Jiang Y Z et al. , Synlett, 1998, 847.
[69 ] Chan A S C, Hu W H, Pai C C et al. , J. Am. Chem. Soc. , 1997, 119, 9570.
[70 ] Hu W H, Yan M , Lau C P et al. , Tetrahedron Lett. , 1999, 40 , 973.
[71 ] Bakos J , Heil B, Marko L , J. Organomet. Chem. , 1983, 253, 249.
[72 ] Zhou H Y, Lu S J , Hou J G et al. , Chem. Lett. , 1996, 339.
[73 ] Zhou H Y, Hou J G, Chen J et al. , J. Organomet. Chem. , 1997, 543, 227.
[74 ] Xie B H, Xia C G, Lu S J et al. , Tetrahedron Lett. , 1998, 39, 7365.
[75 ] Hayashi T , Kawamara N , Ito Y, J. Am. Chem. Soc. , 1987, 109, 7876.
[76 ] Sayo N , Taketomi T , Kumobayashi H et al. , E P 271 311, 1988 (Chem. Abstr. , 1989, 110,39189).
[77 ] 郑晓来(Zheng X L ) , 王艳华(Wang Y H) , 左焕培(Zuo H P) , 分子催化(Journal of Molecular Catalysis ) , 1996, 10 (1) , 70.
[78 ] Parrinello G, Stille J K, J. Am. Chem. Soc. , 1987, 109, 7122.
[79 ] Ishizaki T , EP 544 455, 1993 (Chem. Abstr. , 1993, 119, 181016).
[80 ] Stille J K, Reactive Polymers , 1989, 10, 165.
[81 ] Noyori R, Ohta M , Hsiao Y et al. , J. Am. Chem. Soc. , 1986, 108, 7117.
[82 ] Noyori R, Ohkuma T , Kitamura M , J. Am. Chem. Soc. , 1987, 109, 5856.
[83 ] Chalomer P A , Handbook of Coordination Catalysis in Organic Chemistry , 1986, Chapter, 129.
[84 ] Enev V , Ewers C L J , Harre M et al. , J. Org. Chem. , 1997, 62, 7092.
[85 ] Pye P J , Rossen K, Reamer R A et al. , J. Am. Chem. Soc. , 1997, 119, 6207.
[86 ] Burk M J , Gross M F, Martinez J P, J. A m. Chem. Soc. , 1995, 117, 9375.
[87 ] Noyori R, Takaya H, Acc. Chem. R es. , 1990, 23, 345.
[88 ] Ohta T , Takaya H, Kitamura M et al. , J. Org. Chem. , 1987, 52, 3174.
[89 ] Kitamura M , Okuma T , Inoue S et al. , J. Am. Chem. Soc. , 1988, 110, 629.
[90 ] Noyori R, Ikeda T , Ohkuma T et al. J. Am. Chem. Soc. , 1989, 111, 9134.
[91 ] Spindler F, Pugin B, Blaser H U , Angew. Chem. , Int. Ed. Engl. , 1990, 29, 558.
[92 ] Kotha S, Tetrahedron, 1994, 50, 3639.
[93 ] Kollar L , Wada T , Lautens M , Tetrahedron: Asymmetry , 1992, 3, 1011.
[94 ] Parrinello G, Stille J K, J. Mol. Catal. , 1983, 21, 203.
[95 ] Parrinello G, Stille J K, J. Am. Chem. Soc. , 1987, 109, 7122.
[96 ] Cserepiszucs S, Bakos J , Chem. Commun. , 1997, 6, 635.
[97 ] Naili S, Carpentier J F, Agbossou F et al. , Organometallics, 1995, 14 (1) , 401.
[98 ] Horiuchi T , Ohta T , Shirakawa E et al. , J. Org. Chem. , 1997, 62 (13) , 4285.
[99 ] Nozaki K, Li W G, Horiuchi Y et al. , Tetrahedron Lett. , 1997, 38 (26) , 4611.
[100 ] Horiuchi T , Ohta T , Shirakawa E et al. , Tetrahedron, 1997, 53 (23) , 7795.
[101 ] Alper H, Hamel N , J. Chem. Soc. , Chem. Comm un. , 1990, 135.
[102 ] Alper H, Hamel N , J. Am. Chem. Soc. , 1990, 112, 2803.
[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] 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.
[3] Jie Yu, Liu-Zhu Gong. Discovery and Typical Advances of Chiral Amino Amide Catalysts [J]. Progress in Chemistry, 2020, 32(11): 1729-1744.
[4] 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.
[5] 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.
[6] 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.
[7] Zhiyong Han, Liuzhu Gong*. Asymmetric Organo/Palladium Combined Catalysis [J]. Progress in Chemistry, 2018, 30(5): 505-512.
[8] Jun Luo, YanSong Zheng. Chiral Calixarenes and Their Supramolecular Chirality [J]. Progress in Chemistry, 2018, 30(5): 601-615.
[9] Zhang Yongli, Zhang Rui, Chang Honghong, Wei Wenlong, Li Xing. Asymmetric Carbonyl-ene Reactions Promoted by Chiral Catalysts [J]. Progress in Chemistry, 2014, 26(09): 1492-1505.
[10] Jin Qingxian, Li Jing, Li Xiaogang, Zhang Li, Fang Shaoming, Liu Minghua. Function and Application of Supramolecular Gels：Chiral Molecular Recognition and Asymmetric Catalysis [J]. Progress in Chemistry, 2014, 26(06): 919-930.
[11] Yu Lide, Cui Hanfeng*, Fan Hao, Ren Shuhui, Lin Yan. Chiral Quaternary Phosphonium Salts in Asymmetric Catalysis [J]. Progress in Chemistry, 2013, 25(05): 744-751.
[12] Li Gaowei, Wang Xiaojuan, Zhao Wenxian, Lu Liujie, Liu Guanjun, Wang Mincan. Trost-Type Chiral Semi-Azacrown Ether Ligands in Asymmetric Catalysis [J]. Progress in Chemistry, 2012, 24(0203): 348-360.
[13] Lin Lili, Liu Xiaohua, Feng XIiaoming. Asymmetric Reactions Catalyzed by Chiral Tridentate Schiff Base-Metal Complexes [J]. Progress in Chemistry, 2010, 22(07): 1353-1361.
[14] Xu Lijin Yi Bing Dang Limin Tang Weijun. Asymmetric catalysis in ionic liquids [J]. Progress in Chemistry, 2010, 22(07): 1254-1273.
[15] Liu Ji, Ma Baode, Yang Nianfa, Fan Jinghua. Soluble Polymer-Supported Homogeneous Catalysts [J]. Progress in Chemistry, 2010, 22(07): 1457-1470.