Palladium-Catalyzed Asymmetric Dihydroxylation of 1,3-Dienes with Catechols

被引:11
|
作者
Fan, Tao [1 ,2 ]
Shen, Hong-Cheng [1 ,2 ]
Han, Zhi-Yong [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
KINETIC RESOLUTION; CONJUGATED DIENES; BOND ACTIVATION; ALLYLATION; ALCOHOLS; DIFUNCTIONALIZATION; ENANTIOMERS; LIGANDS; ALKENES;
D O I
10.1002/cjoc.201800540
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
of main observation and conclusion A palladium-catalyzed asymmetric dihydroxylation of 1,3-dienes with catechols is developed using chiral pyridinebis(oxazoline) ligands. Various chiral 2-substituted 1,4-benzodioxanes could be synthesized with moderate to high yields and enantioselectivities from readily available starting materials. The reaction is proposed to proceed through a cascade Wacker-type hydroxypalladation/asymmetric allylation process.
引用
收藏
页码:226 / 232
页数:7
相关论文
共 50 条
  • [31] Palladium-Catalyzed Regio- and Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity
    Zhang, Qinglong
    Dong, Dongfang
    Zi, Weiwei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (37) : 15860 - 15869
  • [32] Palladium-Catalyzed Oxidative Cyclization of Azulene-2-Carboxylic Acids with 1,3-Dienes for the Synthesis of Alkenyl Azulenolactones
    Maeng, Chanyoung
    Yun, Yongjoo
    Son, Jeong-Yu
    Lee, Phil Ho
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) : 2859 - 2864
  • [33] Palladium-Catalyzed Three-Component Reaction of Allenes, Aryl Iodides, and Diazo Compounds: Approach to 1,3-Dienes
    Xiao, Qing
    Wang, Binglong
    Tian, Leiming
    Yang, Yang
    Ma, Jian
    Zhang, Yan
    Chen, Shufeng
    Wang, Jianbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9305 - 9308
  • [34] Synthesis of 1,4-Diarylbuta-1,3-dienes through Palladium-Catalyzed Decarboxylative Coupling of Unsaturated Carboxylic Acids
    Yamashita, Mana
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) : 631 - 636
  • [35] Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
    Yang, Xiao-Hui
    Dong, Vy M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (05) : 1774 - 1777
  • [36] Cu-Catalyzed Asymmetric Dicarboxylation of 1,3-Dienes with CO2
    Gui, Yong-Yuan
    Chen, Xiao-Wang
    Mo, Xiao-Yan
    Yue, Jun-Ping
    Yuan, Rong
    Liu, Yi
    Liao, Li-Li
    Ye, Jian-Heng
    Yu, Da-Gang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (05) : 2919 - 2927
  • [37] Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes
    Sharma, Rakesh K.
    RajanBabu, T. V.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3295 - +
  • [38] Regiodivergent Copper Catalyzed Borocyanation of 1,3-Dienes
    Jia, Tao
    He, Qiong
    Ruscoe, Rebecca E.
    Pulis, Alexander P.
    Procter, David J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (35) : 11305 - 11309
  • [39] Silver-Catalyzed Intermolecular Hydroamination of Alkenes and 1,3-Dienes
    Giner, Xavier
    Najera, Carmen
    SYNLETT, 2009, (19) : 3211 - 3213
  • [40] Nickel Catalyzed Enantioselective 1,4-Hydroamination of 1,3-Dienes
    Wang, Chengdong
    Wang, Xingheng
    Wang, Zheng
    Wang, Xiaoming
    Ding, Kuiling
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, : 18440 - 18450