A Pd-Catalyzed Synthesis of Functionalized Piperidines

被引:28
|
作者
Allen, Benjamin D. W. [1 ]
Connolly, Matthew J. [1 ]
Harrity, Joseph P. A. [1 ]
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
基金
英国工程与自然科学研究理事会;
关键词
annulation; enantioselectivity; Pd catalysis; piperidine; NATURAL-PRODUCT SYNTHESIS; 3+3 ANNELATION; CYCLOADDITION; TRIMETHYLENEMETHANE; HETEROCYCLES; ANNULATIONS; ALLYLATION; STRATEGY; IMINES; ROUTE;
D O I
10.1002/chem.201602586
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A readily available cyclic carbamate 1 functions as a general precursor to a range of functionalized piperidine products via a new Pd-catalyzed annulation strategy. An asymmetric catalytic variant provides a rapid and efficient means to access these heterocycles with high to excellent levels of enantiocontrol. Finally, these richly functionalized compounds are amenable to further chemoselective elaboration.
引用
收藏
页码:12999 / 13003
页数:5
相关论文
共 50 条
  • [31] Synthesis of diaryldifluoromethanes by Pd-catalyzed difluoroalkylation of arylboronic acids
    Gu, Ji-Wei
    Guo, Wen-Hao
    Zhang, Xingang
    [J]. Organic Chemistry Frontiers, 2015, 2 (01): : 38 - 41
  • [32] Pd-Catalyzed Arylperfluoroalkylation of Unactivated Olefins for the Synthesis of Heterocycles
    Zheng, Jinhua
    Chen, Pan
    Yuan, Yaofeng
    Cheng, Jiajia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5790 - 5797
  • [33] Pd-Catalyzed Dehydrative Synthesis of Allylic Amines in Water
    Yu, Jing
    Yan, Xiaoyu
    Liu, Feng
    Zhou, Ying
    Man, Wenxin
    Ma, Xiantao
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (05)
  • [34] Synthesis of Carbazolequinones by Pd-Catalyzed Double Arylation Process
    Li, Xue
    Song, Zirui
    Chen, Xin
    Cai, Yichao
    Liu, Yajie
    Chen, Chunxia
    Peng, Jinsong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (04) : 950 - 958
  • [35] Synthesis of lndolizine Derivatives by Pd-Catalyzed Oxidative Carbonylation
    Xu, Tongyu
    Alper, Howard
    [J]. ORGANIC LETTERS, 2015, 17 (18) : 4526 - 4529
  • [36] Synthesis of resveratrol using Pd-catalyzed bond formation
    Panigot, Michael J.
    Zhu, Xijing
    Hancock, Catherine
    Ward, Amy
    McGuire, Holly
    Strain, Britton
    Anderson, Sierra
    Green, Joshua D.
    Hargrave, Sarah
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [37] Synthesis of poly(aryl ether) by Pd-catalyzed polycondensation
    Shibasaki, Y
    Ueda, M
    [J]. CHEMISTRY LETTERS, 2002, (08) : 794 - 795
  • [38] Pd-catalyzed enantioselective intramolecular α-arylation of α-substituted cyclic ketones: facile synthesis of functionalized chiral spirobicycles
    Fan, Lulu
    Takizawa, Shinobu
    Takeuchi, Yoshiki
    Takenaka, Kazuhiro
    Sasai, Hiroaki
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (17) : 4837 - 4840
  • [39] Heterocycle Synthesis through Pd-Catalyzed Carbonylative Coupling
    Perrone, Serena
    Troisi, Luigino
    Salomone, Antonio
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (29) : 4626 - 4643
  • [40] Synthesis of Diphenylhexatriene by the Pd-Catalyzed Dimerization of Cinnamyl Acetate
    Mesganaw, Tehetena
    Im, G-Yoon J.
    Garg, Neil K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3391 - 3393