Synthesis of α,ω-differently substituted cyclic ethers from carbohydrates by β-fragmentation of alkoxyl radicals

被引：8
|
作者：
Boto, A [1 ]
Hernández, R [1 ]
Suárez, E [1 ]
机构：
[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal de la Laguna 38206, Spain
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期
关键词：
alkoxyl radical; fragmentation carbohydrates; diastereoselective synthesise; alditols; cyclic ethers;
D O I：
10.1016/S0040-4039(02)00123-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The beta-fragmentation of alkoxyl radicals derived from easily available carbohydrates is a mild and efficient procedure to obtain unsymmetrical alpha,omega-disubstituted cyclic ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1821 / 1824
页数：4
相关论文
共 50 条
  • [21] An expeditious and environmentally benign methodology for the synthesis of substituted indoles from cyclic enol ethers and enol lactones
    Singh, Pankajkumar R.
    Surpur, Mandar P.
    Patil, Sachin B.
    TETRAHEDRON LETTERS, 2008, 49 (20) : 3335 - 3340
  • [22] Fragmentation mechanisms from electron -impact of complex cyclic ethers formed in combustion
    Koritzke, Alanna L.
    Frandsen, Kelsey M.
    Christianson, Matthew G.
    Davis, Jacob C.
    Doner, Anna C.
    Larsson, Alexander
    Breda-Nixon, Josiah
    Rotavera, Brandon
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2020, 454
  • [23] FRAGMENTATION OF CARBOHYDRATE ANOMERIC ALKOXY RADICALS - A NEW GENERAL-SYNTHESIS OF CYCLIC KETOSES
    DEARMAS, P
    FRANCISCO, CG
    SUAREZ, E
    TETRAHEDRON LETTERS, 1993, 34 (45) : 7331 - 7334
  • [24] SYNTHESIS OF SUBSTITUTED CROWN ETHERS FROM OLIGOETHYLENE GLYCOLS
    IKEDA, I
    YAMAMURA, S
    NAKATSUJI, Y
    OKAHARA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26): : 5355 - 5358
  • [25] Synthesis of alkenyl-substituted cyclic enol ethers by catalytic ring-closing metathesis of alkynyl ethers
    Clark, JS
    Trevitt, GP
    Boyall, D
    Stammen, B
    CHEMICAL COMMUNICATIONS, 1998, (23) : 2629 - 2630
  • [26] Carbonate synthesis from carbon dioxide and cyclic ethers over methylated nitrogen-substituted mesoporous silica
    Yamazaki, Kiyoyuki
    Moteki, Takahiko
    Ogura, Masaru
    MOLECULAR CATALYSIS, 2018, 454 : 38 - 43
  • [27] Synergistic Acid-Catalyzed Synthesis of N-Aryl-Substituted Azacycles from Anilines and Cyclic Ethers
    Zhang, Zhenbei
    Miao, Chengxia
    Xia, Chungu
    Sun, Wei
    ORGANIC LETTERS, 2016, 18 (07) : 1522 - 1525
  • [28] Fragmentation of carbohydrate anomeric alkoxyl radicals.: A new synthesis of chiral β-lodo azides, vinyl azides, and 2H-azirines
    Alonso-Cruz, CR
    Kennedy, AR
    Rodríguez, MS
    Suárez, E
    ORGANIC LETTERS, 2003, 5 (20) : 3729 - 3732
  • [29] Fragmentation of carbohydrate anomeric alkoxyl radicals.: Synthesis of highly functionalized chiral vinyl sulfones (vol 46, pg 5265, 2005)
    Alonso-Cruz, CR
    León, EI
    Ortiz-López, FJ
    Rodríguez, MS
    Suárez, E
    TETRAHEDRON LETTERS, 2006, 47 (08) : 1359 - 1359
  • [30] STEREOSELECTIVE SYNTHESIS OF NON-CARBOHYDRATES FROM CYCLIC PRECURSORS
    KOHNKE, FH
    STODDART, JF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 32 - CARB
12345