Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins via an Ene Reaction/[2,3]-Rearrangement

被引:72
作者
Bao, Hongli [1 ]
Tambar, Uttam K. [1 ]
机构
[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Div Chem, Dallas, TX 75390 USA
基金
美国国家卫生研究院;
关键词
C-H AMINATION; BONDS; AMIDATION; INSIGHTS; ALKENES; REARRANGEMENT; DIAMINATION; ACETYLENES; ACTIVATION; CARBON;
D O I
10.1021/ja307851b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective allylic am nation. of unactivated terminal olefins represents a direct and attractive strategy for the synthesis of enantioenriched amines. We have developed the first use of a nitrogen. containing reagent and a chiral palladium catalyst to convert unfunctionalized olefins into enantioenriched allylic amines via an ene reaction/[2,3]-rearrangement.
引用
收藏
页码:18495 / 18498
页数:4
相关论文
共 69 条
  • [1] Stereoselective [2,3]-Rearrangements of Amine N-Oxides
    Bao, Hongli
    Qi, Xiangbing
    Tambar, Uttam K.
    [J]. SYNLETT, 2011, (13) : 1789 - 1792
  • [2] Catalytic Enantioselective [2,3]-Rearrangements of Amine N-Oxides
    Bao, Hongli
    Qi, Xiangbing
    Tambar, Uttam K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1206 - 1208
  • [3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [4] Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
  • [5] Aerobic oxidative amination of unactivated alkenes catalyzed by palladium
    Brice, JL
    Harang, JE
    Timokhin, VI
    Anastasi, NR
    Stahl, SS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2868 - 2869
  • [6] Bruckner R., 1991, COMPREHENSIVE ORGANI, V6, P873
  • [7] Allylic amination and 1,2-diamination with a modified diimidoselenium reagent
    Bruncko, M
    Khuong, TAV
    Sharpless, KB
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (04) : 454 - 456
  • [8] Tuneable asymmetric copper-catalysed allylic amination and oxidation reactions
    Clark, JS
    Roche, C
    [J]. CHEMICAL COMMUNICATIONS, 2005, (41) : 5175 - 5177
  • [9] Catalytic C-H amination: the stereoselectivity issue
    Collet, Florence
    Lescot, Camille
    Dauban, Philippe
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1926 - 1936
  • [10] Catalytic C-H amination: recent progress and future directions
    Collet, Florence
    Dodd, Robert H.
    Dauban, Philippe
    [J]. CHEMICAL COMMUNICATIONS, 2009, (34) : 5061 - 5074