Highly regioselective Wittig reactions of cyclic ketones with a stabilized phosphorus ylide under controlled microwave heating

被引：38
|
作者：
Wu, JL
Wu, HF
Wei, SY
Dai, WM [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Lab Asymmetr Catalysis & Synth, Hangzhou 310027, Peoples R China
[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 22期
关键词：
microwave; Wittig; regioselectivity; phosphorus ylide;
D O I：
10.1016/j.tetlet.2004.03.198
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Significant base and temperature effects on the Wittig reactions of cyclohexanones with (carbethoxymethylene)triphenylphosphorane under microwave irradiation were observed. For the Wittig reactions carried out in a domestic microwave oven under solvent-free conditions, the initially formed exo-olefin products isomerized into the thermodynamically more stable endo-olefins due to uncontrolled high reaction temperature. In sharp contrast, under controlled microwave heating, both exo- and endo-olefins have been selectively synthesized by accurately regulating the reaction temperature with or without a base. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4401 / 4404
页数：4
相关论文
共 14 条
  • [1] Microwave-assisted regioselective olefinations of cyclic mono- and di-ketones with a stabilized phosphorus ylide
    Wu, JL
    Li, D
    Wu, HF
    Sun, LJ
    Dai, WM
    TETRAHEDRON, 2006, 62 (19) : 4643 - 4650
  • [2] Theoretical study of the Wittig reaction of cyclic ketones with phosphorus ylide
    Nisha Jarwal
    Pompozhi Protasis Thankachan
    Journal of Molecular Modeling, 2015, 21
  • [3] Theoretical study of the Wittig reaction of cyclic ketones with phosphorus ylide
    Jarwal, Nisha
    Thankachan, Pompozhi Protasis
    JOURNAL OF MOLECULAR MODELING, 2015, 21 (04)
  • [4] Microwave accelerated Wittig reactions of stabilized phosphorus ylides with ketones under solvent-free conditions
    Spinella, A
    Fortunati, T
    Soriente, A
    SYNLETT, 1997, (01) : 93 - &
  • [5] Microwave Accelerated Wittig Reactions of Stabilized Phosphorus Ylides with Ketones under Solvent-Free Conditions
    Synlett, 1 (93):
  • [6] Theoretical study of the Wittig, aza-Wittig and arsa-Wittig reactions of Me3P = XH ylide (X = CH, N and As) with cyclic ketones in the gas phase and solution phase
    Jarwal, Nisha
    Thankachan, Pompozhi Protasis
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2017, 1114 : 65 - 76
  • [7] STEREOSELECTIVE SYNTHESIS OF TRANS-HYDROAZULENE DERIVATIVES BY TANDEM MICHAEL-INTRAMOLECULAR WITTIG REACTIONS OF A CYCLIC PHOSPHONIUM YLIDE WITH ALKYL OR ARYL 1-CYCLOPENTENYL KETONES
    FUJIMOTO, T
    UCHIYAMA, YK
    KODAMA, Y
    OHTA, K
    YAMAMOTO, I
    KAKEHI, A
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26): : 7322 - 7323
  • [8] Efficient solid-phase synthesis of cyclic RGD peptides under controlled microwave heating
    Yamada, Keiichi
    Nagashima, Izuru
    Hachisu, Masakazu
    Matsuo, Ichiro
    Shimizu, Hiroki
    TETRAHEDRON LETTERS, 2012, 53 (09) : 1066 - 1070
  • [9] Fast and selective synthesis of novel cyclic sulfamide HIV-1 protease inhibitors under controlled microwave heating
    Gold, H
    Ax, A
    Vrang, L
    Samuelsson, B
    Karlén, A
    Hallberga, A
    Larhed, M
    TETRAHEDRON, 2006, 62 (19) : 4671 - 4675
  • [10] Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating
    Sadek, Kamal Usef
    Mekheimer, Ramadan Ahmed
    Mohamed, Tahany Mahmoud
    Moustafa, Moustafa Sherief
    Elnagdi, Mohamed Hilmy
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 18 - 24
12