Synthesis and applications of C2-symmetric guanidine bases

被引:125
作者
Allingham, MT
Howard-Jones, A
Murphy, PJ [1 ]
Thomas, DA
Caulkett, PWR
机构
[1] Univ Wales, Dept Chem, Bangor LL57 2UW, Gwynedd, Wales
[2] AstraZeneca, CVGI Dept, Macclesfield SK10 4TG, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
phase transfer; catalysis; guanidine;
D O I
10.1016/j.tetlet.2003.09.162
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of the tetracyclic C-2-symmetric guanidinium salts 5 and 11-13 is reported together with their application to enantioselective transformations. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8677 / 8680
页数:4
相关论文
共 26 条
  • [1] GUANIDINIUM CATALYZED CONJUGATE ADDITION OF PYRROLIDINE TO UNSATURATED LACTONES
    ALCAZAR, V
    MORAN, JR
    DEMENDOZA, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3941 - 3944
  • [2] [Anonymous], 1997, PHASE TRANSFER CATAL
  • [3] Synthesis of novel chiral crown ethers derived from D-glucose and their application to an enantioselective Michael reaction
    Bakó, P
    Bajor, Z
    Toke, L
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (24): : 3651 - 3655
  • [4] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION
    CHINCHILLA, R
    NAJERA, C
    SANCHEZAGULLO, P
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (07) : 1393 - 1402
  • [5] Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism
    Corey, EJ
    Bo, YX
    Busch-Petersen, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 13000 - 13001
  • [6] Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst
    Corey, EJ
    Noe, MC
    Xu, F
    [J]. TETRAHEDRON LETTERS, 1998, 39 (30) : 5347 - 5350
  • [7] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
    Corey, EJ
    Xu, F
    Noe, MC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415
  • [8] Synthesis of a novel C2-symmetric guanidine base
    Howard-Jones, A
    Murphy, PJ
    Thomas, DA
    Caulkett, PWR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1039 - 1041
  • [9] Modified guanidines as chiral superbases: application to asymmetric Michael reaction of glycine imine with acrylate or its related compounds
    Ishikawa, T
    Araki, Y
    Kumamoto, T
    Seki, H
    Fukuda, K
    Isobe, T
    [J]. CHEMICAL COMMUNICATIONS, 2001, (03) : 245 - 246
  • [10] Kita T, 2002, ANGEW CHEM INT EDIT, V41, P2832, DOI 10.1002/1521-3773(20020802)41:15<2832::AID-ANIE2832>3.0.CO