Chiral-at-Metal Octahedral Iridium Catalyst for the Asymmetric Construction of an All-Carbon Quaternary Stereocenter

被引:106
|
作者
Chen, Liang-An [1 ,2 ]
Tang, Xiaojuan [1 ,2 ]
Xi, Jianwei [1 ,2 ]
Xu, Weici [1 ,2 ]
Gong, Lei [1 ,2 ]
Meggers, Eric [1 ,2 ,3 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Dept Biol Chem, Xiamen 361005, Peoples R China
[3] Univ Marburg, Fachbereich Chem, D-35043 Marburg, Germany
关键词
asymmetric catalysis; chirality; hydrogen bonds; iridium; quaternary stereocenter; FRIEDEL-CRAFTS ALKYLATION; ENANTIOSELECTIVE CONSTRUCTION; STEREOGENIC CENTERS; CONJUGATE ADDITION; BOND DONORS; COMPLEXES; ORGANOCATALYSIS; HYDROGENATION; NITROALKENES; POTASSIUM;
D O I
10.1002/anie.201306997
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Metal-templated organocatalysis: The enantioselective formation of an all-carbon quaternary stereocenter is catalyzed by the ligand sphere of an inert bis-cyclometalated iridium complex (see picture). In this complex, the metal-centered chirality serves as the sole source for the effective asymmetric induction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:14021 / 14025
页数:5
相关论文
共 50 条
  • [41] Iridium-Catalyzed Asymmetric Allylic Alkylation of Boron Enolates to Construct Acyclic All-Carbon Quaternary Stereocenters
    Yang, Liu
    Yang, Mengzhi
    Wang, Zhenchao
    Zhao, Wanxiang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [42] Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the a-Position by the Antilla Allylboration
    Chen Yuliang
    He Fengkai
    Wang Siyun
    Jia Dingcheng
    Liu Yaqun
    Huang Yiyong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (12) : 4294 - 4302
  • [43] All-carbon chiral quaternary centers via asymmetric hydrovinylation: Enantioselective synthesis of (-)-desoxyeseroline and related compounds
    RajanBabu, T. V.
    Lim, Hwan Jung
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [44] Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation
    Arao, Takafumi
    Kondo, Kazuhiro
    Aoyama, Toyohiko
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (12) : 1743 - 1747
  • [45] Enantioselective Cyclopropanation of Indoles: Construction of All-Carbon Quaternary Stereocenters
    Oezueduru, Guelsuem
    Schubach, Thea
    Boysen, Mike M. K.
    ORGANIC LETTERS, 2012, 14 (19) : 4990 - 4993
  • [46] Vinylogous propargylation of α,α-dicyanoalkenes: construction of an all-carbon quaternary center
    Lu, Shuhui
    Zhao, Yujie
    Xie, Su
    Li, Wei
    Li, Shi-Wu
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (46) : 21155 - 21158
  • [47] Diastereo- and Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters via Iridium/Europium Bimetallic Catalysis
    Wang, Wei
    Zhang, Fangqing
    Liu, Yangbin
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (39)
  • [48] Enantioselective construction of vicinal all-carbon quaternary centers via catalytic double asymmetric decarboxylative allylation
    Ghosh, Santanu
    Bhunia, Subhajit
    Kakde, Badrinath N.
    De, Subhadip
    Bisai, Alakesh
    CHEMICAL COMMUNICATIONS, 2014, 50 (19) : 2434 - 2437
  • [49] Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter
    Sexton, Mary
    Malachowski, William P.
    Yap, Glenn P. A.
    Rachii, Diana
    Feldman, Greg
    Krasley, Andrew T.
    Chen, Zhilin
    Tran, My Anh
    Wiley, Kalyn
    Matei, Alexandra
    Petersen, Samantha
    Tien, Sabrina Tran
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (02): : 1154 - 1172
  • [50] Organocatalytic asymmetric vinylogous Michael addition of 3-alkylidene oxindoles to α-substituted β-nitroacrylates: facile construction of a chiral all-carbon quaternary center
    Zhong, Yuan
    Ma, Shixiong
    Xu, Zhaoqing
    Chang, Min
    Wang, Rui
    RSC ADVANCES, 2014, 4 (91) : 49930 - 49933