Enantioselective Decarboxylative Amination: Synthesis of Axially Chiral Allenyl Amines

被引：82
作者：
Wan, Baoqiang [1 ]
Ma, Shengming [1 ,2 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 01期
基金：
中国国家自然科学基金;
关键词：
allene; amination; chirality; enantioselectivity; synthetic methods; CATALYZED ASYMMETRIC-SYNTHESIS; ALLYLIC ALKYLATION; GOLD CATALYSIS; ZINC ENOLATE; OPPORTUNITIES; CYCLOADDITION; PHOSPHATES; CHEMISTRY; METALS; ESTERS;
D O I：
10.1002/anie.201204796
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Getting axed: Synthesis of the title amines, bearing functionality (R 1 and R2), involves the enantioselective palladiumcatalyzed decarboxylation of allenyl Ntosylcarbamates. The reaction proceeds smoothly using both the chiral ligands (S)- and (R)-DTBM-Segphos (1) to afford the allenyl amines in good yields and with high enantioseletivities. © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：441 / 445
页数：5
相关论文
共 67 条
  • [1] Cross-Coupling/Cyclization Reactions of Two Different Allenic Moieties
    Alcaide, Benito
    Almendros, Pedro
    del Campo, Teresa Martinez
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) : 5836 - 5842
  • [2] Alcarazo M., 2010, ANGEW CHEM, V122, P2596
  • [3] Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis
    Alcarazo, Manuel
    Stork, Timon
    Anoop, Anakuthil
    Thiel, Walter
    Fuerstner, Alois
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (14) : 2542 - 2546
  • [4] [Anonymous], ANGEW CHEM
  • [5] [Anonymous], 2011, ANGEW CHEM, V123, P9905
  • [6] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes
    Aubert, Corinne
    Fensterbank, Louis
    Garcia, Pierre
    Malacria, Max
    Simonneau, Antoine
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1954 - 1993
  • [7] Pd-Catalyzed Asymmetric Synthesis of N-Allenyl Amides and Their Au-Catalyzed Cycloisomerizative Hydroalkylation: A New Route Toward Enantioenriched Pyrrolidones
    Boutier, Audrey
    Kammerer-Pentier, Claire
    Krause, Norbert
    Prestat, Guillaume
    Poli, Giovanni
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (13) : 3840 - 3844
  • [8] Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes
    Brasholz, Malte
    Reissig, Hans-Ulrich
    Zimmer, Reinhold
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (01) : 45 - 56
  • [9] Braun M, 2000, ANGEW CHEM INT EDIT, V39, P3494, DOI 10.1002/1521-3773(20001002)39:19<3494::AID-ANIE3494>3.0.CO
  • [10] 2-4
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