Palladium-Catalyzed Decarboxylative Three-Component Synthesis of α-Arylglycines: Replacing Boronic with Carboxylic Acids in the Petasis Reaction

被引:10
作者
Diehl, Andreas M. [1 ]
Manolikakes, Georg [1 ]
机构
[1] Tech Univ Kaiserslautern, Dept Chem, Erwin Schrodinger Str Geb 54, D-67663 Kaiserslautern, Germany
关键词
Synthetic methods; Multicomponent reaction; Sulfonamide; Palladium; Amino acid; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; MANNICH REACTION; PALLADATION;
D O I
10.1002/cctc.202000652
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A palladium-catalyzed three-component synthesis of alpha-arylglycines from benzoic acids, sulfonamides and glyoxylic acid is reported. This novel reaction offers straightforward access to the important arylglycine motif in good yields and high structural diversity. By replacing boronic with carboxylic acids as nucleophilic component, this method can be considered as a more sustainable version of the classical Petasis reaction for synthesis of arylglycines.
引用
收藏
页码:3463 / 3466
页数:4
相关论文
共 49 条
  • [41] Bi(OTf)3-catalyzed three-component synthesis of α-amino acid derivatives
    Schneider, Angelika E.
    Beisel, Tamara
    Shemet, Andrej
    Manolikakes, Georg
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (15) : 2356 - 2359
  • [42] Strecker A., 1850, LIEBIGS ANN CHEM, V75, P27, DOI DOI 10.1002/JLAC.18500750103
  • [43] Theoretical and Experimental Investigation of Palladium(II)-Catalyzed Decarboxylative Addition of Arenecarboxylic Acid to Nitrile
    Svensson, Fredrik
    Mane, Rajendra S.
    Savmarker, Jonas
    Larhed, Mats
    Skold, Christian
    [J]. ORGANOMETALLICS, 2013, 32 (02) : 490 - 497
  • [44] Peptide therapeutics: Targeting the undruggable space
    Tsomaia, Natia
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 : 459 - 470
  • [45] Glycopeptide antibiotics from conventional molecules to new derivatives
    Van Bambeke, F
    Van Laethem, Y
    Courvalin, P
    Tulkens, PM
    [J]. DRUGS, 2004, 64 (09) : 913 - 936
  • [46] Asymmetric Strecker Reactions
    Wang, Jun
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMICAL REVIEWS, 2011, 111 (11) : 6947 - 6983
  • [47] Synthesis of 3-Indolylglycine Derivatives via Dinuclear Zinc Catalytic Asymmetric Friedel-Crafts Alkylation Reaction
    Wang, Xin-Wei
    Hua, Yuan-Zhao
    Wang, Min-Can
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) : 9227 - 9234
  • [48] ASYMMETRIC-SYNTHESIS OF ARYLGLYCINES
    WILLIAMS, RM
    HENDRIX, JA
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 889 - 917
  • [49] Reactivity and Synthetic Applications of Multicomponent Petasis Reactions
    Wu, Peng
    Givskov, Michael
    Nielsen, Thomas E.
    [J]. CHEMICAL REVIEWS, 2019, 119 (20) : 11245 - 11290