Copper-catalyzed enantioselective propargylic substitution of propargylic acetates with enamines

被引:18
作者
Wang, Bo [1 ,2 ]
Liu, Chunxiao [1 ]
Guo, Hongchao [2 ]
机构
[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
[2] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
来源
RSC ADVANCES | 2014年 / 4卷 / 95期
关键词
ASYMMETRIC ALLYLIC ALKYLATION; ALLENYLIDENE COMPLEXES; BETA-KETOESTERS; ALCOHOLS; ESTERS; AMINATION; CHEMISTRY; LIGANDS; CATIONS; AMINES;
D O I
10.1039/c4ra09431j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
With the use of chiral tridentate P,N,N ligand, copper-catalyzed enantioselective propargylic substitution of propargylic acetates with enamines has been achieved, giving the corresponding propargylic ketones in high yields and with excellent enantioselectivities.
引用
收藏
页码:53216 / 53219
页数:4
相关论文
共 56 条
  • [1] All Kinds of Reactivity: Recent Breakthroughs in Metal-Catalyzed Alkyne Chemistry
    Anaya de Parrodi, Cecilia
    Walsh, Patrick J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (26) : 4679 - 4682
  • [2] Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives
    Bauer, Eike B.
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (08): : 1131 - 1151
  • [3] Brandsma L., 2004, Synthesis of Acetylenes, Allenes, and Cumulenes: Methods and Techniques
  • [4] Brandsma L., 1988, PREPARATIVE ACETYLEN, V2nd
  • [5] Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis
    Bruneau, C
    Dixneuf, PH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) : 2176 - 2203
  • [6] Bruneau C., 2008, METAL VINYLIDENES AL
  • [7] Allenylidene and Higher Cumulenylidene Complexes
    Cadierno, Victorio
    Gimeno, Jose
    [J]. CHEMICAL REVIEWS, 2009, 109 (08) : 3512 - 3560
  • [8] Enantioselective copper-catalyzed propargylic amination
    Detz, Remko J.
    Delville, Marielle M. E.
    Hiemstra, Henk
    van Maarseveen, Jan H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) : 3777 - 3780
  • [9] Clickphine: A novel and highly versatile P,N ligand class via click chemistry
    Detz, Remko J.
    Arevalo Heras, Silvia
    de Gelder, R.
    van Leeuwen, Piet W. N. M.
    Hiemstra, Henk
    Reek, Joost N. H.
    van Maarseveen, Jan H.
    [J]. ORGANIC LETTERS, 2006, 8 (15) : 3227 - 3230
  • [10] The Nicholas reaction:: A powerful tool for the stereoselective synthesis of bioactive compounds
    Diaz, David D.
    Betancort, Juan M.
    Martin, Victor S.
    [J]. SYNLETT, 2007, (03) : 343 - 359