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
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 45期
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
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共 69 条
  • [11] Recent advances in catalytic intramolecular C-H aminations
    Davies, HML
    Long, MS
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) : 3518 - 3520
  • [12] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion
    Davies, Huw M. L.
    Manning, James R.
    [J]. NATURE, 2008, 451 (7177) : 417 - 424
  • [13] DIRECT REGIOSPECIFIC ALLYLIC AMINATION VIA SILICON INDUCED PERICYCLIC-REACTIONS - A NOVEL SYNTHESIS OF GAMMA-VINYL GABA
    DELERIS, G
    DUNOGUES, J
    GADRAS, A
    [J]. TETRAHEDRON, 1988, 44 (13) : 4243 - 4258
  • [14] High enantioselection in the rearrangement of allylic imidates with ferrocenyl oxazoline catalysts
    Donde, Y
    Overman, LE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (12) : 2933 - 2934
  • [15] Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation
    Du, Haifeng
    Zhao, Baoguo
    Shi, Yian
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8590 - +
  • [16] A Pd(0)-catalyzed diamination of terminal olefins at allylic and homoallylic carbons via formal C-H activation under solvent-free conditions
    Du, Haifeng
    Yuan, Weicheng
    Zhao, Baoguo
    Shi, Yian
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) : 7496 - +
  • [17] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
    Engle, Keary M.
    Mei, Tian-Sheng
    Wasa, Masayuki
    Yu, Jin-Quan
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 788 - 802
  • [18] Expanding the scope of C-H amination through catalyst design
    Espino, CG
    Fiori, KW
    Kim, M
    Du Bois, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) : 15378 - 15379
  • [19] Asymmetric synthesis of active pharmaceutical ingredients
    Farina, Vittorio
    Reeves, Jonathan T.
    Senanayake, Chris H.
    Song, Jinhua J.
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2734 - 2793
  • [20] Catalytic intermolecular amination of C-H bonds: Method development and mechanistic insights
    Fiori, Kristin Williams
    Du Bois, J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (03) : 562 - 568
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