Enantioselective addition of phenyl and alkyl acetylenes to imines catalyzed by chiral Cu(I) complexes

被引:69
|
作者
Benaglia, M [1 ]
Negri, D [1 ]
Dell'Anna, G [1 ]
机构
[1] Politecn Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
propargyl amines; chiral bis-imines; acetylenes addition; chiral ligands; asymmetric catalysis;
D O I
10.1016/j.tetlet.2004.09.138
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective addition of phenyl acetylene and alkyl acetylenes to imines, catalyzed by chiral bis-imines-Cu(1) complexes was studied. A very simple experimental procedure allowed to obtain at room temperature optically active propargyl amines in very good yields and enantioselectivity up to 81%. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8705 / 8708
页数:4
相关论文
共 50 条
  • [41] Enantioselective hydrosilylation of prochiral ketones catalyzed by chiral BINAP-copper(I) complexes
    Issenhuth, Jean-Thomas
    Dagorne, Samuel
    Bellemin-Laponnaz, Stephane
    COMPTES RENDUS CHIMIE, 2010, 13 (03) : 353 - 357
  • [42] Enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of chiral phosphine–phosphite ligands
    Kyoko Nozaki
    Hidemasa Takaya
    Tamejiro Hiyama
    Topics in Catalysis, 1997, 4 : 175 - 185
  • [43] Highly enantioselective aza-Henry reaction of N-tosyl imines catalyzed by N,N'-dioxide-Cu(I) complexes
    Zhou, Hui
    Peng, Dan
    Qin, Bo
    Hou, Zongrui
    Liu, Xiaohua
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26): : 10302 - 10304
  • [44] Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene
    Wei, CM
    Li, CJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) : 5638 - 5639
  • [45] α-Chiral Acetylenes Having an All-Carbon Quaternary Center: Phase Transfer Catalyzed Enantioselective α Alkylation of α-Alkyl-α-alkynyl Esters
    Hashimoto, Takuya
    Sakata, Kazuki
    Maruoka, Keiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (27) : 5014 - 5017
  • [46] Prediction of enantioselectivity in thiol addition to imines catalyzed by chiral phosphoric acids
    Yu, Xinliang
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2022, 35 (06)
  • [47] Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
    Puglisi, Alessandra
    Benaglia, Maurizio
    Annunziata, Rita
    Rossi, Davide
    TETRAHEDRON-ASYMMETRY, 2008, 19 (19) : 2258 - 2264
  • [48] Enantioselective fluorination reactions catalyzed by chiral palladium complexes
    Hamashima, Yoshitaka
    Sodeoka, Mikiko
    SYNLETT, 2006, (10) : 1467 - 1478
  • [49] Enantioselective Addition of Thiols to Imines Catalyzed by Thiourea-Quaternary Ammonium Salts
    Wang, Hong-Yu
    Zhang, Jia-Xing
    Cao, Dong-Dong
    Zhao, Gang
    ACS CATALYSIS, 2013, 3 (10): : 2218 - 2221
  • [50] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY CHIRAL HYDROXY AMINAL
    ASAMI, M
    INOUE, S
    CHEMISTRY LETTERS, 1991, (04) : 685 - 688