Asymmetric Transformations via C-C Bond Cleavage

被引:34
|
作者
Souillart, Laetitia [1 ]
Parker, Evelyne [1 ]
Cramer, Nicolai [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Sch Basic Sci, Inst Chem Sci & Engn, Lab Asymmetr Catalysis & Synth, CH-1015 Lausanne, Switzerland
来源
C-C BOND ACTIVATION | 2014年 / 346卷
关键词
beta-Carbon elimination; Asymmetric catalysis; C-C cleavage; Ligands; Oxidative insertion; Palladium; Rhodium; Strain release; PALLADIUM-CATALYZED ARYLATION; TERT-CYCLOBUTANOLS; INTRAMOLECULAR ARYLCYANATION; ENANTIOSELECTIVE SYNTHESIS; 3,3-DISUBSTITUTED OXINDOLES; SUBSTITUTED PHENOLS; HOMOALLYL ALCOHOLS; OLEFIN INSERTION; RING EXPANSION; RHODIUM;
D O I
10.1007/128_2013_505
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic asymmetric transformations operating by carbon-carbon (C-C) bonds cleavages have emerged as intriguing strategies to access transient organometallic species from different reaction pathways. The reactions and the applicable substrate range have expanded considerably over the last decade. This overview covers the main developments in this field. A major focus is placed on beta-carbon eliminations of strained tert-alcohols and related processes which have been shown to be particularly versatile in a broad range of transformations. Furthermore, exciting developments of asymmetric processes based on direct oxidative C-C bond insertion reactions, for instance into the acyl C-C bond of ketones or the C-CN bond of nitriles, are discussed.
引用
收藏
页码:163 / 193
页数:31
相关论文
共 50 条
  • [1] Direct Alkenylation of Allylbenzenes via Chelation-Assisted C-C Bond Cleavage
    Onodera, Shunsuke
    Ishikawa, Soya
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (31) : 9788 - 9792
  • [2] Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage
    Chen, Chenhui
    Wang, Hongliang
    Sun, Yufeng
    Cui, Jiayan
    Xie, Jianbo
    Shi, Yang
    Yu, Shijia
    Hong, Xin
    Lu, Zhan
    ISCIENCE, 2020, 23 (04)
  • [3] Ruthenium- and Rhodium-Catalyzed Strain-Driven Cleavage and Reconstruction of the C-C Bond
    Kondo, Teruyuki
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (07) : 1232 - 1242
  • [4] DECARBOXYLATIVE C-C BOND CLEAVAGE REACTIONS VIA OXAPALLADACYCLES
    Kimura, Masanari
    Kohno, Tomohiko
    Toyoda, Kei
    Mori, Takamichi
    HETEROCYCLES, 2010, 82 (01) : 281 - 287
  • [5] Potential of Metal-Catalyzed C-C Single Bond Cleavage for Organic Synthesis
    Murakami, Masahiro
    Ishida, Naoki
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (42) : 13759 - 13769
  • [6] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [7] Direct oxidative arylation via rhodium-catalyzed C-C bond cleavage of secondary alcohols with arylsilanes
    Chen, Kang
    Li, Hu
    Li, Yang
    Zhang, Xi-Sha
    Lei, Zhi-Quan
    Shi, Zhang-Jie
    CHEMICAL SCIENCE, 2012, 3 (05) : 1645 - 1649
  • [8] Enantioselective Rhodium-Catalyzed C-C Bond Activations
    Seiser, Tobias
    Cramer, Nicolai
    CHIMIA, 2010, 64 (03) : 153 - 156
  • [9] Synthesis of atropisomeric chiral MeOBIPHEP analogues via Pd-catalyzed P-C coupling - applications to asymmetric Rh-catalyzed C-C bond formations in water
    Leseurre, Lucie
    d'Herouville, Florent Le Boucher
    Millet, Anthony
    Genet, Jean-Pierre
    Scalone, Michelangelo
    Michelet, Veronique
    CATALYSIS COMMUNICATIONS, 2015, 69 : 129 - 132
  • [10] Metal free access to quinolines via C-C bond cleavage of styrenes
    Deshidi, Ramesh
    Devari, Shekaraiah
    Shah, Bhahwal Ali
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (05): : 515 - 519