Structure-selectivity studies on catalysts for the phase-transfer catalysed asymmetric alkylation of glycine imine esters

被引:65
作者
Lygo, B [1 ]
Crosby, J
Lowdon, TR
Wainwright, PG
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] AstraZeneca, Proc R&D, Macclesfield SK10 2NA, Cheshire, England
[3] Hickson & Welch Ltd, Castleford WF10 2JT, W Yorkshire, England
[4] Univ Salford, Dept Chem, Salford M5 4WT, Lancs, England
关键词
cinchona alkaloid; phase-transfer; asymmetric catalysis; amino acid;
D O I
10.1016/S0040-4020(01)00093-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper, we describe the synthesis of a series of chiral quaternary ammonium salts with core structures that are closely related to the cinchona alkaloid, cinchonine. By employing these salts as asymmetric phase-transfer agents in the benzylation of a glycine imine, an optimal catalyst structure is identified. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2391 / 2402
页数:12
相关论文
共 38 条
  • [21] Martyres D, 1999, SYNLETT, P1508
  • [22] Nelson A, 1999, ANGEW CHEM INT EDIT, V38, P1583, DOI 10.1002/(SICI)1521-3773(19990601)38:11<1583::AID-ANIE1583>3.0.CO
  • [23] 2-E
  • [24] O'Donnell M. J., 1996, ACS SYM SER, V659, P124
  • [25] An efficient homogeneous catalytic enantioselective synthesis of α-amino acid derivatives
    O'Donnell, MJ
    Delgado, F
    Hostettler, C
    Schwesinger, R
    [J]. TETRAHEDRON LETTERS, 1998, 39 (48) : 8775 - 8778
  • [26] Enantioselective solid-phase synthesis of α-amino acid derivatives
    O'Donnell, MJ
    Delgado, F
    Pottorf, RS
    [J]. TETRAHEDRON, 1999, 55 (20) : 6347 - 6362
  • [27] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF ALPHA-METHYL AMINO-ACID DERIVATIVES BY PHASE-TRANSFER CATALYSIS
    ODONNELL, MJ
    WU, SD
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (05) : 591 - 594
  • [28] THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS BY PHASE-TRANSFER CATALYSIS
    ODONNELL, MJ
    BENNETT, WD
    WU, SD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) : 2353 - 2355
  • [29] A NEW ACTIVE CATALYST SPECIES FOR ENANTIOSELECTIVE ALKYLATION BY PHASE-TRANSFER CATALYSIS
    ODONNELL, MJ
    WU, SD
    HUFFMAN, JC
    [J]. TETRAHEDRON, 1994, 50 (15) : 4507 - 4518
  • [30] ODONNELL MJ, 1997, ACS S SERIES, V659