Enantio selective addition of alkynes to imines in ionic liquids

被引：35
作者：
Rosa, JN
Santos, AG
Afonso, CAM [1 ]
机构：
[1] Inst Super Tecn, CQFM, Dept Engn Quim, P-1049001 Lisbon, Portugal
[2] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, REQUIMTE,CQFB, P-2829516 Caparica, Portugal
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2004年 / 214卷 / 01期
关键词：
ionic liquids; reuse; recycling; enantioselective catalysis; imines; propargylamines;
D O I：
10.1016/j.molcata.2003.10.065
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The enantioselective alkyne-imine addition catalysed by copper(I)-bis(oxazoline) (box) can be efficiently performed in the ionic liquid 1-n-butyl-3-methyl imidazolium bis(trifluoromethylsulfonyl)imide [bmim][NTf2]. Several substrates were tested and the reuse of the catalytic CuOTf/(box) was carried out for six cycles allowing high overall yield (87%) and enantioselectivity (first cycle 94%, sixth cycle 89%). (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码：161 / 165
页数：5
相关论文
共 82 条
  • [1] Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains
    Abbott, AP
    Capper, G
    Davies, DL
    Munro, HL
    Rasheed, RK
    Tambyrajah, V
    [J]. CHEMICAL COMMUNICATIONS, 2001, (19) : 2010 - 2011
  • [2] The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids
    Aggarwal, A
    Lancaster, NL
    Sethi, AR
    Welton, T
    [J]. GREEN CHEMISTRY, 2002, 4 (05) : 517 - 520
  • [3] Unexpected side reactions of imidazolium-based ionic liquids in the base-catalysed Baylis-Hillman reaction
    Aggarwal, VK
    Emme, I
    Mereu, A
    [J]. CHEMICAL COMMUNICATIONS, 2002, (15) : 1612 - 1613
  • [4] Three-component one-pot synthesis of functionalised (Z)-4-benzylidene (and alkenylidene) pyrrolidines
    Azoulay, S
    Monteiro, N
    Balme, G
    [J]. TETRAHEDRON LETTERS, 2002, 43 (51) : 9311 - 9314
  • [5] Supercritical fluids in heterogeneous catalysis
    Baiker, A
    [J]. CHEMICAL REVIEWS, 1999, 99 (02) : 453 - 473
  • [6] CO2 capture by a task-specific ionic liquid
    Bates, ED
    Mayton, RD
    Ntai, I
    Davis, JH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) : 926 - 927
  • [7] Using soluble polymers to recover catalysts and ligands
    Bergbreiter, DE
    [J]. CHEMICAL REVIEWS, 2002, 102 (10) : 3345 - 3383
  • [8] Recent progress in the asymmetric synthesis of α-substituted propargylamines
    Blanchet, J
    Bonin, M
    Micouin, L
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (05) : 467 - 492
  • [9] Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines
    Blanchet, J
    Bonin, M
    Micouin, L
    Husson, HP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) : 6423 - 6426
  • [10] ON THE AZETIDIN-2-ONE RING FORMATION - A H-1-NMR INVESTIGATION
    BOLOGNESE, A
    DIURNO, MV
    MAZZONI, O
    GIORDANO, F
    [J]. TETRAHEDRON, 1991, 47 (35) : 7417 - 7428
123456789