中文
Announcement
More
Progress in Chemistry 2004, Vol. 16 Issue (04): 603- Previous Articles   Next Articles

• Review •

Advances of Rhodium-Catalyzed Enantioselective Hydrogenation of Functional Olefins--The Thriving of Monodentate Phosphorous Ligands

Zeng Qingli1,2**;Mi Aiqiao3;Jiang Yaozhong3   

  1. (1.Department of Pharmacy, Sichuan University, Chengdu 610041, China; 2.Institute of New Medicine, Di'ao Group, Chengdu 610041, China; 3.Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China)

  • Received: Revised: Online: Published:
  • Contact: Zeng Qingle
PDF ( 1884 ) Cited
Export

EndNote

Ris

BibTeX

The whole historical progress in rhodium-catalyzed enantioselective hydrogenation of fuctional olefins is reviewed briefly. Specially, the recently thriving of monodentate phosphorous ligands is discussed in detail. A construc-tive prospect about the research is given.

CLC Number: 

[ 1 ] Stinson S C. C&EN , 2002 , 80 (23) : 43 —57
[ 2 ] 林国强, 陈耀全, 陈新滋, 李月明. 手性合成———不对称反应及其应用. 北京: 科学出版社出版, 2000. 250 —290
[ 3 ] 殷元骐, 蒋耀忠主编. 不对称催化反应进展. 北京: 科学出版社出版, 2000. 1 —68
[ 4 ] Knowles W S. Acc. Chem. Res. , 1983 , 16 : 106 —112
[ 5 ] Blaser H U , Jalett H P , Lottenbach W, Studer M. J . Am.Chem. Soc. , 2000 , 122 (51) : 12675 —12682
[ 6 ] Morrison J D. Chiral Catalysis-Asymmetric Synthesis , Vol . 5 . Or lando : Academic , 1985. 1 —101
[ 7 ] Young J F , Osborne J A , Jardine F A , Wilkinson , G. Chem.Commun. , 1965 , 131 —132
[ 8 ] Korpium O , Lewis R A , Chickos J , Mislow K. J . Am. Chem.Soc. , 1968 , 90 : 4842
[ 9 ] Knowles J D , Sabacky M J . J . Chem. Soc. , Chem. Commun. ,1968 , 1445
[10] Horner L , Siegel H , Buthe H. Angew. Chem. Int . Ed. Engl . ,1968 , 7 : 942
[11] Morrison J D , Burnett R E , Aguiar A M, Morrow C J , Phillips C.J . Am. Chem. Soc. , 1971 , 93 : 1301
[12] (a) Dang T P , Kagan H B. J . Chem. Soc. , Chem. Commun. ,1971 , 481 ; (b) Kagan H B , Dang T P. J . Am. Chem. Soc. ,1972 , 94 : 6429 —6433
[13] Knowles W S. Adv. Synth. Catal . , 2003 , 345 (1/2) : 3 —13
[14] Miyashita A , Yasuda A , Takaya H , Toriumi K, Ito T, Souchi T,Noyori R. J . Am. Chem. Soc. , 1980 , 102 : 7932 —7934
[15] Noyori R. Adv. Synth. Catal . , 2003 , 345 (1P2) : 15 —32
[16] 野依良治(Noyori R) . 化学通报( Chemistry) , 2002 , ( 6) :363 —372
[17] Noyori R , Hashiguchi S. Acc. Chem. Res. , 1997 , 30 (2) : 97 —102
[18] Noyori R , Ohkuma T. Angew. Chem. Int . Ed. , 2001 , 40 (1) :40 —73
[19] Ohkuma T, Noyori R. Comprehensive Asymmetric Catalysis.(eds. Jacobsen E N , Pfaltz A , Yamamoto H) Berlin : Springer ,1999. Vol . I , 199 —246
[20] Noyori R , Ohkuma T. Angew. Chem. Int . Ed. , 2001 , 40 (1) :40 —73
[21] Burk M J , Feaster J E , Harlow R L. Organometallics , 1990 , 9 :2653 —2655
[22] Burk M J . J . Am. Chem. Soc. , 1991 , 113 : 8519 —8521
[23] Burk M J , Feaster J E. J . Am. Chem. Soc. , 1992 , 114 :6266 —6267
[24] Burk M J , Feaster J E , Nugent W A , Harlow R L. J . Am.Chem. Soc. , 1993 , 115 : 10125 —10138
[25] Burk M J , Allen J G, Kiesman W F. J . Am. Chem. Soc. ,1998 , 120 (4) : 657 —663
[26] Burk M J , Kalberg C S , Pizzano A. J . Am. Chem. Soc. , 1998 ,120 (18) : 4345 —4353
[27] Tang W, Zhang X. Chem. Rev. , 2003 ,103 (8) : 3029 —3070
[28] Zhu G, Cao P , Jiang Q , Zhang X. J . Am. Chem. Soc. , 1997 ,119 : 1799 —1800
[29] Jiang Q Z, Jiang Y T, Zhang X M, et al . Angew. Chem. Int .Ed. Engl . , 1998 , 37 : 1100 —1103
[30] Xiao D , Zhang Z, Zhang X. Org. Lett . , 1999 , 1 (10) : 1679 —1681
[31] Xiao D , Zhang X. Angew. Chem. Int . Ed. , 2001 , 40 (18) :3425 —3428
[32] Chan A S C , Pluth J J , Halpern J . J . Am. Chem. Soc. , 1980 ,102 : 5952 —5954
[33] Chan A S C , Halpern J . J . Am. Chem. Soc. , 1980 , 102 (2) :838 —840
[34] Chan A S C , Hu W, Pai C C , Lau C P , Jiang Y, Mi A , Yan M,Sun J , Lou R , Deng J . J . Am. Chem. Soc. , 1997 , 119 :9570 —9571
[35] Chen Y, Li X, Tong S , Choi M C K, Chan A S C. Tetrahedron Lett . , 1999 , 40 (5) : 957 —960
[36] Zhang F Y, Kwok W H , Chan A S C. Tetrahedron : Asymmetry ,2001 , 12 : 2337 —2342
[37] Zhang F Y, Pai C C , Chan A S C. J . Am. Chem. Soc. , 1998 ,120 (23) : 5808 —5809
[38] Pai C C , Lin C W, Lin C C , Chen C C , Chan A S C. J . Am.Chem. Soc. , 2000 , 122 : 11513 —11514
[39] Fu G C. Chem. Innov. , 2000 , 3 —5
[40] Pye P J , Rossen K, Reamer R A , et al . J . Am. Chem. Soc. ,1997 ; 119 (26) : 6207 —6208
[41] Qiao S , Fu G C. J . Org. Chem. , 1998 , 63 (13) : 4168 —4169
[42] Imamoto T, Oshiki T, Onozawa T, Kusumoto T, Sato K. J . Am.Chem. Soc. , 1990 , 112 : 5244 —5252
[43] (a) Imamoto T, Watanabe J , Wada Y, et al . J . Am. Chem.Soc. , 1998 , 120 (7) : 1635 —1636 ; (b) Gridnev I D , Yamanoi Y, Higashi N , et al . Adv. Synth. Catal . , 2001 , 343 : 118 —136 ; ( c) Ohashi A , Imamoto T. Org. Lett . , 2001 , 3 ( 3) :373 —375 ; (d) Yasutake M, Gridnev I D , Higashi N , Imamoto T. Org. Lett . , 2001 , 3 (11) : 1701 —1704
[44] (a) Ohashi A , Imamoto T. Org. Lett . , 2001 , 3 (3) : 373 —375 ;(b) Yasutake M, Gridnev I D , Higashi N , Imamoto T. Org.Lett . , 2001 , 3 (11) : 1701 —1704
[45] Ostermeier M, PrieβJ , Helmchen G. Angew. Chem. Int . Ed. ,2002 , 41 (4) : 612 —614
[46] Bakos J , Toth I , Heil B. Tetrahedron Lett . , 1984 , 25 ( 43) :4965 —4966
[47] RajanBabu T V , Ayers T A , Halliday G A , et al . J . Org.Chem. , 1997 , 62 (17) : 6012 —6028
[48] Jiang Y, Xue S , Li Z, et al . Tetrahedron : Asymmetry , 1998 , 9(18) : 3185 —3189
[49] Mi A , Lou R , Jiang Y, et al . SynLett . 1998 , 8 : 847 —848
[50] Lou R , Mi A , Jiang Y, et al . Tetrahedron , 2000 , 56 ( 32) :5857 —5864
[51] Xie Y, Lou R , Jiang Y. Tetrahedron : Asymmetry , 2000 , 11 (7) :1487 —1494
[52] Chen G, Deng Y, Mi A , et al . Tetrahedron : Asymmetry , 2001 ,12 (11) : 1567 —1572
[53] Gong L , Chen G, Mi A , Jiang Y, et al . Tetrahedron : Asymmetry , 2000 , 11 (21) : 4297 —4302
[54] Gong L , Chen G, Mi A , Jiang Y, et al . Tetrahedron : Asymmetry , 2000 , 11 (21) : 4297 —4302
[55] Zhang X, Gong L , Mi A , et al . Tetrahedron Lett . , 2001 , 42(36) : 6369 —6372
[56] Zhang H L , Zhang X M, Mi A Q , Jiang Y Z, et al . Org. Lett . ,2002 , 4 (8) : 1399 —1402
[57] Zhang X M, Mi A Q , Jiang Y Z, et al . J . Org. Chem. , 2003 ,68 : 4322 —4329
[58] Reetz M T, Gosberg A , Goddard R , Kyung S H. Chem. Commun. , 1998 , 19 : 2077 —2078
[59] Reetz M T, Neugebauer T. Angew. Chem. Int . Ed. , 1999 , 38(1/2) : 179 —181
[60] Huttenloch O , Spieler J , Waldmann H. Chem. Eur. J . , 2001 , 7(3) : 671 —675
[61] Burk M J , Feaster J E , Harlow R L. Tetrahedron : Asymmetry ,1991 , 2 (7) : 569 —592
[62] Guillen F , Fiaud J C. Tetrahedron Lett . , 1999 , 40 (15) : 2939—2942
[63] Komarov I V , Bêrner A. Angew. Chem. Int . Ed. , 2001 , 40(7) : 1197 —1200
[64] Claver C , Fernandez E , Pringle P , et al . Chem. Commun. ,2000 , 961 —962
[65] Hulst R , Vries N K, Feringa , B L. Tetrahedron : Asymmetry ,1994 , 5 (4) : 699 —708
[66] Feringa B L. Acc. Chem. Res. , 2000 , 33 : 346 —353
[67] Van den Berg M, Minnaard A J , Feringa B L , et al . J . Am.Chem. Soc. , 2000 , 122 (46) : 11539 —11540
[68] Pena D , Minnaard A J , Vries J G, Feringa B L. J . Am. Chem.Soc. , 2002 , 124 (49) : 14552 —14553
[69] Reetz M T, Mehler G. Angew. Chem. Int . Ed. , 2000 , 39 (21) :3889 —3890
[70] Chen W, Xiao J . Tetrahedron Lett . , 2001 , 42 (15) : 2897 —2900
[71] Zeng Q , Liu H , Cui X, Mi A , Jiang Y, Li X, Choi M C K,Chan A S C. Tetrahedron : Asymmetry , 2002 , 13 (2) : 115 —117
[72] Zeng Q , Liu H , Mi A , Jiang Y, Li X, Choi M C K, Chan A S C. Tetrahedron , 2002 , 58 (43) : 8799 —8803
[73] Fu Y, Xie J H , Zhou Q L , et al . Chem. Commun. , 2002 , (5) :480 —481
[74] Hu A G, Fu Y, Zhou Q L , et al . Angew. Chem. Int . Ed. ,2002 , 41 (13) : 2348 —2350
[75] Xie J H , Wang L X, Zhou Q L , et al . J . Am. Chem. Soc. ,2003 , 125 : 4404 —4405
[76] Halpern J . Science , 1982 , 217 (4558) : 401 —407
[77] Brown J M. Comprehensive Asymmetric Catalysis. (eds. Jacobsen E N , Pfaltz A , Yamamoto H) Berlin : Springer , 1999. Vol . I ,121 —182
[78] Landis C R , Feldgus S. Angew. Chem. Int . Ed. , 2000 , 39(16) : 2863 —2866
[79] Jacobsen E N , Pfaltz A , Yamamoto H ( eds. ) . Comprehensive Asymmetric Catalysis. Berlin : Springer , 1999. Vol . III , 1425 —1469

[1] Yuewen Shao, Qingyang Li, Xinyi Dong, Mengjiao Fan, Lijun Zhang, Xun Hu. Heterogeneous Bifunctional Catalysts for Catalyzing Conversion of Levulinic Acid to γ-Valerolactone [J]. Progress in Chemistry, 2023, 35(4): 593-605.
[2] 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.
[3] 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.
[4] Xin Lin, Fanfu Guan, Jialin Wen, Pan-Lin Shao, Xumu Zhang. Synthesis of Chiral Tridentate Ligands with a Ferrocene Framework and Their Applications in Ir-Catalyzed Asymmetric Hydrogenation [J]. Progress in Chemistry, 2020, 32(11): 1680-1696.
[5] Jie Yu, Liu-Zhu Gong. Discovery and Typical Advances of Chiral Amino Amide Catalysts [J]. Progress in Chemistry, 2020, 32(11): 1729-1744.
[6] Lihua Qian, Guojun Lan, Xiaoyan Liu, Qingfeng Ye, Ying Li. Heterogeneous Catalysts for Biomass-Based Molecules Aqueous-Phase Catalytic Hydrogenation [J]. Progress in Chemistry, 2019, 31(8): 1075-1085.
[7] 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.
[8] 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.
[9] 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.
[10] Zhiyong Han, Liuzhu Gong*. Asymmetric Organo/Palladium Combined Catalysis [J]. Progress in Chemistry, 2018, 30(5): 505-512.
[11] Jun Luo, YanSong Zheng. Chiral Calixarenes and Their Supramolecular Chirality [J]. Progress in Chemistry, 2018, 30(5): 601-615.
[12] 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.
[13] Xiao Longqiang, Chen Cheng, Chen Fangjuan, Liu Lijian. Carbene Polymerization of α-Carbonyl Diazo Compounds [J]. Progress in Chemistry, 2014, 26(09): 1506-1515.
[14] 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.
[15] Zhang Lei, Tu Qian, Chen Xuenian, Liu Pu. Nano Metal Catalysts in Dehydrogenation of Ammonia Borane [J]. Progress in Chemistry, 2014, 26(05): 749-755.