Preparation and use of MeO-PEG-supported chiral diphosphine ligands: soluble polymer-supported catalysts for asymmetric hydrogenation

被引:58
作者
Fan, QH [1 ]
Deng, GJ
Lin, CC
Chan, ASC
机构
[1] Chinese Acad Sci, Inst Chem, LMRSS, Ctr Mol Sci, Beijing 100080, Peoples R China
[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1016/S0957-4166(01)00210-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two new chiral MeO-PEG-supported (R)-BINAP and (3R,4R)-Pyrphos ligands were synthesized and employed in the Ru(II)- and Rh(I)-catalyzed asymmetric hydrogenation of 2-(6 ' -methoxy-2 ' -naphthyl)propenoic acid 5 and prochiral enamides 10. The results showed that these new soluble polymeric catalysts exhibited high catalytic activity and enantioselectivity. Enantiomeric excesses (e.e.s) in the ranges 90-96% and 86-96% were achieved in the hydrogenation of 5 and 10, respectively. Furthermore, these catalysts could he recovered easily and the recycled catalysts were shown to maintain their efficiency in subsequent reactions. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1241 / 1247
页数:7
相关论文
共 26 条
  • [1] The use of soluble polymers to effect homogeneous catalyst separation and reuse
    Bergbreiter, DE
    [J]. CATALYSIS TODAY, 1998, 42 (04) : 389 - 397
  • [2] Asymmetric dihydroxylation with MeO-polyethyleneglycol-bound ligands
    Bolm, C
    Gerlach, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07): : 741 - 743
  • [3] Efficient polymer-supported Sharpless alkene epoxidation catalyst
    Canali, L
    Karjalainen, JK
    Sherrington, DC
    Hormi, O
    [J]. CHEMICAL COMMUNICATIONS, 1997, (01) : 123 - 124
  • [4] Novel spiro phosphinite ligands and their application in homogeneous catalytic hydrogenation reactions
    Chan, ASC
    Hu, WH
    Pai, CC
    Lau, CP
    Jiang, YZ
    Mi, AQ
    Yan, M
    Sun, J
    Lou, RL
    Deng, JG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) : 9570 - 9571
  • [5] CHAN ASC, 1992, Patent No. 5144050
  • [6] Synthesis, characterization and application of Ru(BINAP)(Acac)(MNAA)(MeOH), a highly effective catalyst for the asymmetric hydrogenation of 2-(6′-methoxynaphth-2′-yl)acrylic acid
    Chen, CC
    Huang, TT
    Lin, CW
    Cao, R
    Chan, ASC
    Wong, WT
    [J]. INORGANICA CHIMICA ACTA, 1998, 270 (1-2) : 247 - 251
  • [7] Highly effective soluble polymer-supported catalysts for asymmetric hydrogenation
    Fan, QH
    Ren, CY
    Yeung, CH
    Hu, WH
    Chan, ASC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) : 7407 - 7408
  • [8] A polymer-enlarged homogeneously soluble oxazaborolidine catalyst for the asymmetric reduction of ketones by borane
    Felder, M
    Giffels, G
    Wandrey, C
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1975 - 1977
  • [9] Polymer enlarged oxazaborolidines in a membrane reactor: enhancing effectivity by retention of the homogeneous catalyst
    Giffels, G
    Beliczey, J
    Felder, M
    Kragl, U
    [J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 691 - 696
  • [10] Aza-bis(oxazolines): New chiral ligands for asymmetric catalysis
    Glos, M
    Reiser, O
    [J]. ORGANIC LETTERS, 2000, 2 (14) : 2045 - 2048