Organocatalyzed cascade reactions of carbohydrates - a direct access to C-glycosides

被引:15
|
作者
Voigt, Benjamin [1 ]
Mahrwald, Rainer [1 ]
机构
[1] Humboldt Univ, Dept Chem, D-12489 Berlin, Germany
关键词
ONE-STEP SYNTHESIS; CARBON-CHAIN; CONVENIENT; DERIVATIVES; VERSATILE; KETONES; SYSTEM; SUGARS; ROUTE;
D O I
10.1039/c3cc48120d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An organocatalyzed transformation to elongate unprotected carbohydrates is described. This operationally simple methodology is based on a Knoevenagel-oxa-Michael cascade. This reaction is catalyzed by proline and DBU. Products were obtained with exceptional high degrees of stereoselectivity.
引用
下载
收藏
页码:817 / 819
页数:3
相关论文
共 50 条
  • [1] Amine-Catalyzed Cascade Reactions of Unprotected and Unactivated Carbohydrates: Direct Access to C-Glycosides
    Witte, Swjatoslaw N. R.
    Voigt, Benjamin
    Mahrwald, Rainer
    SYNTHESIS-STUTTGART, 2015, 47 (15): : 2249 - 2255
  • [2] Cascade Reactions of Unprotected Ketoses with Ketones - A Stereoselective Access to C-Glycosides
    Richter, Celin
    Krumrey, Michael
    Klaue, Kristin
    Mahrwald, Rainer
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (31) : 5309 - 5320
  • [3] Organocatalyzed synthesis of fluorinated C-glycosides
    Altiti, Ahmad
    Bachan, Stewart
    Mootoo, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [4] PALLADIUM CATALYZED-REACTIONS OF UNSATURATED CARBOHYDRATES - A ROUTE TO C-GLYCOSIDES
    ENGELBRECHT, GJ
    HOLZAPFEL, CW
    HETEROCYCLES, 1991, 32 (07) : 1267 - 1272
  • [5] Organophotocatalytic access to C-glycosides: multicomponent coupling reactions using glycosyl bromides
    Sawada, Naoya
    Yu, Ziyi
    Takinami, Hiryu
    Inoue, Daichi
    Ghosh, Titli
    Sasaki, Norihiko
    Nokami, Toshiki
    Taniguchi, Tsuyoshi
    Abe, Manabu
    Koike, Takashi
    CHEMICAL COMMUNICATIONS, 2024, 60 (66)
  • [6] Anodic Coupling Reactions and the Synthesis of C-Glycosides
    Xu, Guoxi
    Moeller, Kevin D.
    ORGANIC LETTERS, 2010, 12 (11) : 2590 - 2593
  • [7] REACTIONS OF GLYCOSYL FLUORIDES - SYNTHESIS OF C-GLYCOSIDES
    NICOLAOU, KC
    DOLLE, RE
    CHUCHOLOWSKI, A
    RANDALL, JL
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (17) : 1153 - 1154
  • [8] Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides
    Demeng Xie
    Wei Zeng
    Jian Yang
    Xiaofeng Ma
    Nature Communications, 15 (1)
  • [9] New and easy access to C-glycosides of glucosamine and mannosamine
    Cipolla, L
    Lay, L
    Nicotra, F
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19): : 6678 - 6681
  • [10] New and Easy Access to C-Glycosides of Glucosamine and Mannosamine
    Dipartimento di Chimica Organica, Univ. Degli Studi di Milano, CNR Ctro. Stud. Sulle Sostanze O. N., Via Venezian 21, 20133 Milano, Italy
    J. Org. Chem., 19 (6678-6681):