Palladium-Catalyzed Stereocontrolled Synthesis of Aryl- C -Glycosides from Arylboronic Acids and Glycal Enones Through 1,4-Conjugate Addition Reactions

被引：0
|
作者：
Singh, Adesh Kumar [1 ]
Venkatesh, Rapelly [2 ]
Kandasamy, Jeyakumar [1 ,2 ]
机构：
[1] Indian Inst Technol BHU, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[2] Pondicherry Univ, Dept Chem, Pondicherry 605014, India
来源：
SYNTHESIS-STUTTGART | 2024年 / 56卷 / 07期
关键词：
glycosides; aryl-; C; -glycosides; 2-deoxy-aryl-; glycal enones; synthetic methods; GLYCOSYLATION; ARENES;
D O I：
10.1055/a-2179-8669
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,4-Conjugate addition of arylboronic acids to the glycal enones delivered 2-deoxy-alpha-aryl-C-glycosides in good yields. The reaction was catalyzed by palladium acetate in the presence of trifluoroacetic acid and 1,10-phenanthroline. A wide range of glycal enones derived from D-glucal, D-galactal, and D-rhamnal participated in the coupling reaction with different arylboronic acids smoothly. Different protecting groups including benzyl, acetyl, pivaloyl, and benzoyl were compatible under optimized conditions.
引用
收藏
页码：1167 / 1174
页数：8
相关论文
共 50 条
  • [21] A Mild, One-Pot Synthesis of Arylamines via Palladium-Catalyzed Addition of Aryl Aldehydes with Amines and Arylboronic Acids in Water
    Yu, Ajuan
    Wu, Yangjie
    Cheng, Baoli
    Wei, Kun
    Li, Jingya
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 767 - 771
  • [22] Palladium-catalyzed synthesis of diarylbenzenes from coupling reactions between equal amount of diiodoarenes and arylboronic acids
    Jincheng Mao
    Ran Li
    Yue He
    Xiaojiang Yang
    Dingli Wang
    Yang Zhang
    Russian Journal of Applied Chemistry, 2016, 89 : 663 - 669
  • [23] A CONCISE SYNTHESIS OF (-)-DIHYDROPROTOLICHESTERINIC ACID VIA CONSECUTIVE STEREOCONTROLLED 1,4-CONJUGATE ADDITION AND SYN-ALDOL CONDENSATION-REACTIONS
    BANKS, MR
    DAWSON, IM
    GOSNEY, I
    HODGSON, PKG
    THORBURN, P
    TETRAHEDRON LETTERS, 1995, 36 (20) : 3567 - 3570
  • [24] Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers
    Van Zeeland, Ryan
    Stanley, Levi M.
    ACS CATALYSIS, 2015, 5 (09): : 5203 - 5206
  • [25] Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4-and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones
    de Gracia Retamosa, Maria
    Alvarez-Casao, Yolanda
    Matador, Esteban
    Gomez, Angela
    Monge, David
    Fernandez, Rosario
    Lassaletta, Jose M.
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (01) : 176 - 184
  • [26] Synthesis of Furanosyl C-1 Glycals through Palladium-Catalyzed Reactions of a Furanosyl 2,3-Anhydro-exo-glycal
    Gomez, Ana M.
    Pedregosa, Ana
    Barrio, Aitor
    Valverde, Serafin
    Cristobal Lopez, J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (27) : 4627 - 4636
  • [27] Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using 2-Chloroimidazolium Chloride as a Coupling Reagent
    Zheng, Wei-Xiang
    Zhong, Jing
    Yang, Yi-Ting
    Luobu, Meluze
    Zhang, Yan
    Wang, Yuan-Hua
    Wang, Qi-Wei
    SYNTHESIS-STUTTGART, 2022, 54 (19): : 4371 - 4380
  • [28] Stereoselective C-glycoside formation by a rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acetylated enones derived from glycals
    Ramnauth, J
    Poulin, O
    Bratovanov, SS
    Rakhit, S
    Maddaford, SP
    ORGANIC LETTERS, 2001, 3 (16) : 2571 - 2573
  • [29] Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1H-Benzotriazoles with Arylboronic Acids
    Singh, Manish K.
    Lakshman, Mahesh K.
    CHEMCATCHEM, 2015, 7 (24) : 4156 - 4162
  • [30] Palladium-catalyzed C(sp3)-H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids
    Chen, Kai
    Li, Xin
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (02): : 204 - 208
12345