One-pot synthesis of β-N-glycosyl imidazole analogues via a palladium-catalysed decarboxylative allylation

被引:25
|
作者
Xiang, Shaohua [1 ]
He, Jingxi [1 ]
Ma, Jimei [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
ALLYLIC ALKYLATION; C-GLYCOSYLATION; ASPARAGINE CONJUGATE; BOND FORMATION; GLYCALS; KETONES; GLYCOBIOLOGY; CYCLIZATION; ACCESS;
D O I
10.1039/c3cc48041k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise and highly efficient strategy for the synthesis of N-glycosyl imidazole analogues is reported. This reaction is based on a palladium catalysed decarboxylative allylation and three steps, namely, carbamation, decarboxylation and allylation are involved. All the substrates can afford the desired products with excellent yields and selectivities.
引用
收藏
页码:4222 / 4224
页数:3
相关论文
共 50 条
  • [21] Palladium on Carbon-Catalyzed One-Pot N-Arylindole Synthesis: Intramolecular Aromatic Amination, Aromatization, and Intermolecular Aromatic Amination
    Monguchi, Yasunari
    Marumoto, Takahisa
    Takamatsu, Haruki
    Sawama, Yoshinari
    Sajiki, Hironao
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) : 1866 - 1872
  • [22] Synthesis of polycyclic substituted vinylarenes via a one-pot intramolecular aryl alkylation-N-tosylhydrazone insertion reaction
    Wu, Xin-Xing
    Zhou, Ping-Xin
    Wang, Li-Jing
    Xu, Peng-Fei
    Liang, Yong-Min
    CHEMICAL COMMUNICATIONS, 2014, 50 (29) : 3882 - 3884
  • [23] One-Pot Three-Component Synthesis of Phenanthrenes via Palladium-Catalyzed Catellani and Retro-Diels-Alder Reactions
    Hao, Tianxin
    Gao, Wei
    Yuan, Sitian
    Liu, Yi
    Li, Yiqing
    Fu, Yang
    Ding, Qiuping
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15) : 10426 - 10433
  • [24] One-Pot Synthesis of Less Accessible N-Boc-Propargylic Amines through BF3 -Catalyzed Alkynylation and Allylation Using Boronic Esters
    Yasumoto, Kento
    Kano, Taichi
    Maruoka, Keiji
    ORGANIC LETTERS, 2019, 21 (09) : 3214 - 3217
  • [25] Palladium-Catalyzed One-Pot Synthesis of N-Formylaniline Derivatives Using Oxalic Acid as a Dual Carbon Monoxide and Hydrogen Donor
    Pootheri, Nithin
    Lee, Sunwoo
    ORGANIC LETTERS, 2024, 26 (43) : 9407 - 9412
  • [26] One-pot, three-component synthesis of novel δ-sultam scaffolds via N-sulfonylation-intramolecular Michael sequences
    Ghandi, Mehdi
    Nazari, Seyed Hadi
    Bozcheloei, Abolfazl Hasani
    Sadeghzadeh, Masoud
    Kia, Reza
    TETRAHEDRON LETTERS, 2011, 52 (49) : 6613 - 6615
  • [27] One-Pot Synthesis of Highly Substituted Allenylidene Derivatives via Palladium- or Nickel-Catalyzed Tandem Michael Addition-Cyclization Reaction
    Shi, Yun
    Huang, Jing
    Yang, Yan-Fang
    Wu, Lu-Yong
    Niu, Yan-Ning
    Huo, Peng-Fei
    Liu, Xue-Yuan
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 141 - 146
  • [28] One-Pot Synthesis of N-(Phosphorylmethyl)Pyrrolidines via Acid-Catalyzed Cascade Elimination/Cyclization/Friedel–Crafts Reaction
    Liliya I. Vagapova
    Alexander R. Burilov
    Almir S. Gazizov
    Julia K. Voronina
    Igor A. Litvinov
    Essan M. Mahrous
    David Virieux
    Jean-Luс Pirat
    Kiryll V. Matylitskii
    Mikhail A. Pudovik
    Chemistry of Heterocyclic Compounds, 2020, 56 : 542 - 547
  • [29] Ruthenium-catalysed one-pot regio- and diastereoselective synthesis of pyrrolo[1,2-a]indoles via cascade C-H functionalization/annulation
    Singh, Sukhdev
    Butani, Himanshu H.
    Vachhani, Dipak D.
    Shah, Anamik
    Van der Eycken, Erik V.
    CHEMICAL COMMUNICATIONS, 2017, 53 (78) : 10812 - 10815
  • [30] Enantioselective Synthesis of gem-Diaryl Benzofuran-3(2H)-ones via One-Pot Asymmetric Rhodium/Palladium Relay Catalysis
    Zhang, Zong-Feng
    Zhu, Dong-Xing
    Chen, Wen-Wen
    Xu, Bin
    Xu, Ming-Hua
    ORGANIC LETTERS, 2017, 19 (10) : 2726 - 2729