Asymmetric Transformations via C-C Bond Cleavage

被引:32
|
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
下载
收藏
页码:163 / 193
页数:31
相关论文
共 50 条
  • [11] Palladium-catalysed asymmetric arylation of tert-cyclobutanols via enantioselective C-C bond cleavage
    Nishimura, T
    Matsumura, S
    Maeda, Y
    Uemura, S
    CHEMICAL COMMUNICATIONS, 2002, (01) : 50 - 51
  • [12] C-C Bond Cleavage in Aromatic Nitration
    Hu Da-Hua
    Zhu Hai-Bin
    Gou Shao-Hua
    CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2008, 24 (11) : 1777 - 1781
  • [13] Construction of C-C Bond via C-N and C-O Cleavage
    Pang, Xiaobo
    He, Rong-De
    Shu, Xing-Zhong
    SYNLETT, 2020, 31 (07) : 635 - 640
  • [14] 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
  • [15] Rhodium-catalyzed alkenylation of allylbenzenes via C-C bond cleavage
    Kakiuchi, Fumitoshi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [16] Efficient trifluoromethylation via the cyclopropanation of allenes and subsequent C-C bond cleavage
    Tang, Yang
    Yu, Qiong
    Ma, Shengming
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (09): : 1762 - 1767
  • [17] Once cleaved C-C bond was reformed: Reversible C-C bond cleavage of dihydroindenyltitanium complexes
    Takahashi, Tamotsu
    Song, Zhiyi
    Hsieh, Yi-Fang
    Nakajima, Kiyohiko
    Kanno, Ken-Ichiro
    Journal of the American Chemical Society, 2008, 130 (46): : 15236 - 15237
  • [18] Once Cleaved C-C Bond Was Reformed: Reversible C-C Bond Cleavage of Dihydroindenyltitanium Complexes
    Takahashi, Tamotsu
    Song, Zhiyi
    Hsieh, Yi-Fang
    Nakajima, Kiyohiko
    Kanno, Ken-ichiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) : 15236 - +
  • [19] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
    Dong, Guangbin
    TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
  • [20] Oxynitrilases for asymmetric C-C bond formation
    Johnson, DV
    Zabelinskaja-Mackova, AA
    Griengl, H
    CURRENT OPINION IN CHEMICAL BIOLOGY, 2000, 4 (01) : 103 - 109