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
收藏
页码:163 / 193
页数:31
相关论文
共 50 条
  • [1] 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
    [J]. ISCIENCE, 2020, 23 (04)
  • [2] DECARBOXYLATIVE C-C BOND CLEAVAGE REACTIONS VIA OXAPALLADACYCLES
    Kimura, Masanari
    Kohno, Tomohiko
    Toyoda, Kei
    Mori, Takamichi
    [J]. HETEROCYCLES, 2010, 82 (01) : 281 - 287
  • [3] Oxidative C-C bond cleavage of lignin via electrocatalysis
    Huang, Jinshu
    Jian, Yumei
    Zhou, Min
    Wu, Hongguo
    [J]. FRONTIERS IN CHEMISTRY, 2022, 10
  • [4] Ring Opening of Methylenecycloalkenes via the C-C Bond Cleavage
    Necas, David
    Kotora, Martin
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5261 - 5263
  • [5] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    [J]. CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [6] Toward Value-Added Chemicals from Carbohydrates via C-C Bond Cleavage and Coupling Transformations
    Zhang, Rui
    Zhang, Junhua
    Liu, Huai
    Jiang, Zhicheng
    Liu, Xudong
    Wang, Wei
    Peng, Lincai
    Hu, Changwei
    [J]. ACS CATALYSIS, 2024, 14 (07) : 5167 - 5197
  • [7] Selective Dealkenylative Functionalization of Styrenes via C-C Bond Cleavage
    Liu, Jianzhong
    Pan, Jun
    Luo, Xiao
    Qiu, Xu
    Zhang, Cheng
    Jiao, Ning
    [J]. RESEARCH, 2020, 2020
  • [8] Amidation of β-Keto Sulfonyl Fluorides via C-C Bond Cleavage
    Liang, Hui
    Liu, Qian
    Zhao, Xueyan
    He, Tianyu
    Luo, Jinyue
    Huang, Shenlin
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (27)
  • [9] Stereoselective cyclopropanation of enamides via C-C bond cleavage of cyclopropenes
    Chen, Jie
    Han, Jiabin
    Wu, Tao
    Zhang, Jian
    Li, Meng
    Xu, Ying
    Zhang, Jinli
    Jiao, Yongjuan
    Yang, Yanhui
    Jiang, Yaojia
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (07) : 1820 - 1825
  • [10] Serendipitous Synthesis of Pyridoquinazolinones via an Oxidative C-C Bond Cleavage
    Brendel, Matthias
    Sakhare, Priyanka R.
    Dahiya, Gaurav
    Subramanian, Parthasarathi
    Kaliappan, Krishna P.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 8102 - 8110