Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

被引：29
|
作者：
Li, Jiagen [1 ]
Wang, Ming [1 ]
Jiang, Xuefeng [1 ,2 ]
机构：
[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 23期
关键词：
RESEMBLE GRANDFATHER GLUCOSE; 2,3-UNSATURATED SUGARS; C-ARYL; CHEMICAL-SYNTHESIS; GLYCOSIDES; EFFICIENT; PROGENY; FACILE; GLYCOPEPTIDES; CARBOHYDRATE;
D O I：
10.1021/acs.orglett.1c03302
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on alpha-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl alpha-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of alpha-sulfoxide-rhamnoside and alpha-sulfoxide-glucoside, respectively.
引用
收藏
页码：9053 / 9057
页数：5
相关论文
共 50 条
  • [11] A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation
    Jung, Youngeun
    Kim, Ikyon
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (14) : 4331 - 4335
  • [12] First quinine-based aryl phosphite: synthesis and application in the Pd-catalyzed enantioselective rearrangement of allylic thiocarbamate
    Bondarev, OG
    Gavrilov, KN
    Tsarev, VN
    Davankov, VA
    Gais, HJ
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (09) : 1748 - 1750
  • [13] Stereodivergent synthesis of 1,4-bifunctional compounds by regio- and diastereoselective Pd-catalyzed allylic substitution reaction
    Maezaki, Naoyoshi
    Yano, Masahiro
    Hirose, Yuki
    Itoh, Yoshikazu
    Tanaka, Tetsuaki
    TETRAHEDRON, 2006, 62 (44) : 10361 - 10378
  • [14] First quinine-based aryl phosphite: synthesis and application in the Pd-catalyzed enantioselective rearrangement of allylic thiocarbamate
    O. G. Bondarev
    K. N. Gavrilov
    V. N. Tsarev
    V. A. Davankov
    H.-J. Gais
    Russian Chemical Bulletin, 2002, 51 : 1748 - 1750
  • [15] Pd-Catalyzed Asymmetric Hydrogenolysis Rearrangement of Allylic Esters to Access Axially Chiral Olefins
    Shao, Bing-Ru
    Jiang, Wen-Feng
    Wang, Chen
    Shi, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (07)
  • [16] Chiral carbon-sulfur center formation via Pd-catalyzed asymmetric allylic thioetherification: synthesis of allylic thioethers
    Cai, Junmei
    Cai, Juewang
    Zheng, Purui
    Wang, Xiaorong
    Zhao, Xiaoming
    RSC ADVANCES, 2017, 7 (01): : 256 - 259
  • [17] Synthesis of allylic sulfonic acids via regioselective Pd-catalyzed allylic substitutions of Na2SO3
    Liu, Wei
    Zhao, Xiaoming
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6800 - 6802
  • [18] Pd-Catalyzed Allylic Alkynylation of Allylic Acetates with Terminal Alkynes
    Yang, Qingjing
    Zhou, Yongyun
    Chen, Jingchao
    He, Xiaobo
    Xu, Jianbin
    Kwong, Fuk Yee
    Fan, Baomin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (24) : 5330 - 5333
  • [19] Synthesis of chiral unsaturated aminolactones using Pd-catalyzed allylic amination
    Kallinen, Annukka
    Tois, Jan
    Sjoholm, Rainer
    Franzen, Robert
    TETRAHEDRON-ASYMMETRY, 2010, 21 (19) : 2367 - 2371
  • [20] Ni- and Pd-Catalyzed Synthesis of Substituted and Functionalized Allylic Boronates
    Zhang, Ping
    Roundtree, Ian A.
    Morken, James P.
    ORGANIC LETTERS, 2012, 14 (06) : 1416 - 1419
12345