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
  • [21] C-GLYCOSIDES OF TAMARIND LEAVES
    BHATIA, VK
    GUPTA, SR
    SESHADRI, TR
    CURRENT SCIENCE, 1964, 33 (19): : 581 - &
  • [22] C-GLYCOSIDES OF PARKINSONIA ACULEATA
    BHATIA, VK
    GUPTA, SR
    SESHADRI, TR
    CURRENT SCIENCE, 1965, 34 (22): : 634 - &
  • [23] Synthesis of nojirimycin C-glycosides
    Cipolla, L
    Palma, A
    La Ferla, B
    Nicotra, F
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (19): : 2161 - 2165
  • [24] C-Glycosides of visnagin analogues
    El Telbani, E
    El Desoly, S
    Hammad, MA
    Hassan, AR
    Rahman, ARHA
    Schmidt, RR
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (11) : 2317 - 2322
  • [25] C-GLYCOSIDES OF TAMARIND LEAVES
    BHATIA, VK
    GUPTA, SR
    SESHADRI, TR
    PHYTOCHEMISTRY, 1966, 5 (01) : 177 - &
  • [26] A Mitsunobu route to C-glycosides
    Pasetto, Paolo
    Walczak, Matthew C.
    TETRAHEDRON, 2009, 65 (41) : 8468 - 8477
  • [27] NEW SYNTHESIS OF C-GLYCOSIDES
    CZERNECKI, S
    GRUY, F
    TETRAHEDRON LETTERS, 1981, 22 (05) : 437 - 440
  • [28] Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions
    Tong, Wenli
    Wan, Jie-Ping
    Liu, Jianchao
    Organic Chemistry Frontiers, 2024, 11 (23) : 6918 - 6941
  • [29] SYNTHESIS OF NEW C-GLYCOSIDES
    ZHDANOV, IA
    DOROFEENKO, IN
    KOROLCHENKO, GA
    BOGDANOVA, GV
    DOKLADY AKADEMII NAUK SSSR, 1963, 152 (01): : 102 - &
  • [30] Organocatalyzed Direct Glycosylation of Unprotected and Unactivated Carbohydrates
    Schmalisch, Sebastian
    Mahrwald, Rainer
    ORGANIC LETTERS, 2013, 15 (22) : 5854 - 5857