Chiral β-amino acid derivatives via asymmetric hydrogenation

被引:94
作者
Drexler, HJ [1 ]
You, JS [1 ]
Zhang, SL [1 ]
Fischer, C [1 ]
Baumann, W [1 ]
Spannenberg, A [1 ]
Heller, D [1 ]
机构
[1] Univ Rostock, Inst Organ Katalyseforsch, D-18055 Rostock, Germany
关键词
D O I
10.1021/op034011z
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This contribution gives an overview of the synthesis of chiral b-amino acids via asymmetric hydrogenation of the corresponding dehydroamino derivatives. Literature results are discussed regarding substrate synthesis and catalyst performance and how it is affected by substrate and catalyst structure as well as experimental parameters. A tentative mechanistic concept for the hydrogenation step is also presented.
引用
收藏
页码:355 / 361
页数:7
相关论文
共 59 条
  • [1] SYNTHESIS OF GEOMETRICAL-ISOMERS OF BETA-ARYLAMIDOACRYLIC ESTERS
    ABERHART, DJ
    LIN, HJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (18) : 3749 - 3751
  • [2] ACHIWA K, 1978, TETRAHEDRON LETT, P1119
  • [3] Enantioselective catalysis in fine chemicals production
    Blaser, HU
    Spindler, F
    Studer, A
    [J]. APPLIED CATALYSIS A-GENERAL, 2001, 221 (1-2) : 119 - 143
  • [4] Selective hydrogenation for fine chemicals: Recent trends and new developments
    Blaser, HU
    Malan, C
    Pugin, B
    Spindler, F
    Steiner, H
    Studer, M
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) : 103 - 151
  • [5] An expedient method for resolution of 3-amino-3-(3′-pyridyl)propionic acid and related compounds
    Boesch, H
    Cesco-Cancian, S
    Hecker, LR
    Hoekstra, WJ
    Justus, M
    Maryanoff, CA
    Scott, L
    Shah, RD
    Solms, G
    Sorgi, KL
    Stefanick, SM
    Thurnheer, U
    Villani, FJ
    Walker, DG
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (01) : 23 - 27
  • [6] The economic use of precious chiral diphosphine ligands-DuPHOS and its rhodium(I) COD and NBD complexes
    Börner, A
    Heller, D
    [J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 223 - 225
  • [7] Brown J. M, 1999, COMPREHENSIVE ASYMME, VI, P121
  • [8] Asymmetric synthesis of β-pyridyl-β-amino acid derivatives
    Bull, SD
    Davies, SG
    Fox, DJ
    Gianotti, M
    Kelly, PM
    Pierres, C
    Savory, ED
    Smith, AD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16): : 1858 - 1868
  • [9] Rh-DuPHOS-catalyzed enantioselective hydrogenation of enol esters.: Application to the synthesis of highly enantioenriched α-hydroxy esters and 1,2-diols
    Burk, MJ
    Kalberg, CS
    Pizzano, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4345 - 4353
  • [10] Me-DuPHOS-Rh-catalyzed asymmetric synthesis of the pivotal glutarate intermediate for candoxatril
    Burk, MJ
    Bienewald, F
    Challenger, S
    Derrick, A
    Ramsden, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3290 - 3298