STEREOSELECTIVE CARBOHYDRATE SYNTHESIS VIA PALLADIUM HYDROXIDE CATALYZED EPOXIDE HYDROGENOLYSIS

被引：0
|
作者：
GARCIA, JG [1 ]
VOLL, RJ [1 ]
YOUNATHAN, ES [1 ]
机构：
[1] LOUISIANA STATE UNIV,DEPT BIOCHEM,BATON ROUGE,LA 70803
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 39期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2,5:3,4-Dianhydro-D-altritol (1) reacts with lithium aluminum hydride to produce a 50:50 mixture of the epimeric alcohols (2) and (3) in fairly good yield. However, when 1 is catalytically hydrogenated in the presence of palladium hydroxide on charcoal (Pearlman's catalyst), the ratio of epimers formed changes to 99:1 (2:3) as determined by GC of the corresponding acetylated derivative compounds. The stereochemistry of the epimers has been determined by NMR spectroscopy.
引用
收藏
页码：5273 / 5276
页数：4
相关论文
共 50 条
  • [1] STEREOSELECTIVE CARBOHYDRATE SYNTHESIS VIA PALLADIUM HYDROXIDE CATALYZED EPOXIDE HYDROGENOLYSIS
    GARCIA, JG
    VOLL, RJ
    YOUNATHAN, ES
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 74 - ORGN
  • [2] STEREOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES VIA PALLADIUM-CATALYZED REACTIONS
    BACKVALL, JE
    VAGBERG, JO
    ZERCHER, C
    GENET, JP
    DENIS, A
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24): : 5430 - 5435
  • [3] Stereoselective synthesis of allylic sulfones via palladium-catalyzed hydrosulfonylation of cyclopropenes
    Wang, Suliang
    Li, Xuening
    Song, Jian
    Fang, Xianjie
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [4] Stereoselective synthesis via palladium-catalyzed intramolecular bis-silylation
    Suginome, M
    Ito, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (11) : 1040 - 1051
  • [5] Stereoselective Spirolactam Synthesis via Palladium Catalyzed Arylative Allene Carbocyclization Cascades
    Li, Meiling
    Dixon, Darren J.
    ORGANIC LETTERS, 2010, 12 (17) : 3784 - 3787
  • [6] STEREOSELECTIVE ANNULATIONS VIA PALLADIUM-CATALYZED REACTIONS
    BACKVALL, JE
    NEW JOURNAL OF CHEMISTRY, 1990, 14 (6-7) : 447 - 452
  • [7] Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions
    Yanada, R
    Obika, S
    Inokuma, T
    Yanada, K
    Yamashita, M
    Ohta, S
    Takemoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6972 - 6975
  • [8] FACILE SYNTHESIS OF (-)-SERRICORNIN BY MEANS OF PALLADIUM-CATALYZED HYDROGENOLYSIS OF ALKENYLOXIRANES
    SHIMIZU, I
    HAYASHI, K
    IDE, N
    OSHIMA, M
    TETRAHEDRON, 1991, 47 (18-19) : 2991 - 2998
  • [9] Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions
    Wolfe, John P.
    SYNLETT, 2008, (19) : 2913 - 2937
  • [10] A novel stereoselective synthesis of maleate derivatives via palladium-catalyzed dicarboalkoxylation of terminal alkynes
    Li, JH
    Jiang, HF
    Jia, LQ
    SYNTHETIC COMMUNICATIONS, 1999, 29 (21) : 3733 - 3738
12345