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
  • [1] Diastereoselective Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to -Substituted Cyclic Enones
    Gao, Ang
    Liu, Xiu-Yan
    Ding, Chang-Hua
    Hou, Xue-Long
    SYNLETT, 2017, 28 (20) : 2829 - 2832
  • [2] Simple palladacyclic and platinacyclic catalysts for the 1,4-conjugate addition of arylboronic acids and arylsiloxanes to enones
    Bedford, Robin B.
    Betham, Michael
    Charmant, Jonathan P. H.
    Haddow, Mairi F.
    Orpen, A. Guy
    Pilarski, Lukasz T.
    Coles, Simon J.
    Hursthouse, Michael B.
    ORGANOMETALLICS, 2007, 26 (25) : 6346 - 6353
  • [3] The first examples of rhodium-catalyzed 1,4-conjugate addition reactions of arylboronic acids with ethenesulfonamides
    Zilaout, Hicham
    van den Hoogenband, Adri
    de Vries, Jelle
    Lange, Jos H. M.
    Terpstra, Jan Willem
    TETRAHEDRON LETTERS, 2011, 52 (45) : 5934 - 5939
  • [4] Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones
    Holder, Jeffrey C.
    Goodman, Emmett D.
    Kikushima, Kotaro
    Gatti, Michele
    Marziale, Alexander N.
    Stoltz, Brian M.
    TETRAHEDRON, 2015, 71 (35) : 5781 - 5792
  • [5] Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones
    Boeser, Cornelia L.
    Holder, Jeffrey C.
    Taylor, Buck L. H.
    Houk, K. N.
    Stoltz, Brian M.
    Zare, Richard N.
    CHEMICAL SCIENCE, 2015, 6 (03) : 1917 - 1922
  • [6] Rhodium-catalyzed conjugate addition of aryl- or 1-alkenylboronic acids to enones
    Sakai, M
    Hayashi, H
    Miyaura, N
    ORGANOMETALLICS, 1997, 16 (20) : 4229 - 4231
  • [7] Rhodium-catalyzed conjugate addition of aryl- or 1-alkenylboronic acids to enones
    Organometallics, 20 (X-4231):
  • [8] Mechanism and Enantioselectivity in Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β-Substituted Cyclic Enones: Insights from Computation and Experiment
    Holder, Jeffrey C.
    Zou, Lufeng
    Marziale, Alexander N.
    Liu, Peng
    Lan, Yu
    Gatti, Michele
    Kikushima, Kotaro
    Houk, K. N.
    Stoltz, Brian M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (40) : 14996 - 15007
  • [9] Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones
    Takaya, Y
    Ogasawara, M
    Hayashi, T
    Sakai, M
    Miyaura, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5579 - 5580
  • [10] Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using EEDQ
    Kwon, Young Bum
    Choi, Bo Ram
    Lee, Seung Hwan
    Seo, Jin-soo
    Yoon, Cheol Min
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (09) : 2672 - 2674
12345