Synthesis of cyclopentenones from cyclopropanes and silyl ynol ethers

被引：61
|
作者：
Qi, Xiangbing [1 ]
Ready, Joseph M. [1 ]
机构：
[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 37期
关键词：
cycloaddition; cyclopentenones; cyclopropanes; ynols;
D O I：
10.1002/anie.200801957
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Exploiting an opening: Lewis acid promoted ring-opening of donor-acceptor cyclopropanes generates a 1,3-zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri-, tetra-, and penta-substituted cyclopentenones in high yield. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7068 / 7070
页数：3
相关论文
共 50 条
  • [41] Pd-catalyzed addition of boronic acids to ynol ethers: a highly regio- and stereoselective synthesis of trisubstituted vinyl ethers
    Bai, Yihui
    Yin, Jing
    Kong, Wei
    Mao, Mengyi
    Zhu, Gangguo
    CHEMICAL COMMUNICATIONS, 2013, 49 (69) : 7650 - 7652
  • [42] Transition-Metal-Free Synthesis of Ynol Ethers and Thioynol Ethers via Displacement at sp Centers: A Revised Mechanistic Pathway
    Gray, Vincent James
    Cuthbertson, James
    Wilden, Jonathan D.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5869 - 5874
  • [43] DYOTROPIC REARRANGEMENTS .7. SYNTHESIS AND THERMAL REARRANGEMENT OF (SILYL)METHYL SILYL ETHERS
    REETZ, MT
    KLIMENT, M
    PLACHKY, M
    CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (08): : 2716 - 2727
  • [44] REACTIVE ENOLATES FROM ENOL SILYL ETHERS
    KUWAJIMA, I
    NAKAMURA, E
    ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (06) : 181 - 187
  • [45] Selective deprotection of either alkyl or aryl silyl ethers from aryl, alkyl bis-silyl ethers
    Ankala, SV
    Fenteany, G
    TETRAHEDRON LETTERS, 2002, 43 (27) : 4729 - 4732
  • [46] Progress towards the synthesis of papuaforin A:: selective formation of α-bromoenones from silyl enol ethers
    Kraus, George A.
    Jeon, Insik
    TETRAHEDRON LETTERS, 2008, 49 (02) : 286 - 288
  • [47] One-Pot, Telescoped Aryl Nitrile Synthesis from Benzylic Silyl Ethers
    Hamada, Shohei
    Kubozono, Suzuka
    Sakamoto, Kaori
    Yano, Kyoko
    Tanaka, Yuka
    Kobayashi, Yusuke
    Furuta, Takumi
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (04): : 1597 - 1604
  • [48] Synthesis of esters from silyl ethers and acyl chlorides: Catalysis by quaternary ammonium chlorides
    Brandange, S
    Leijonmarck, H
    Minassie, T
    ACTA CHEMICA SCANDINAVICA, 1997, 51 (09): : 953 - 957
  • [49] SYNTHESIS OF ALPHA-OXO SULFINES FROM ENOL SILYL ETHERS AND THIONYL CHLORIDE
    LENZ, BG
    REGELING, H
    VANROZENDAAL, HLM
    ZWANENBURG, B
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16): : 2930 - 2934
  • [50] Generation of Nickel Siloxycarbene Complexes from Acylsilanes for the Catalytic Synthesis of Silyl Enol Ethers
    Matsuura, Akihisa
    Ito, Yuri
    Inagaki, Tetsuya
    Kodama, Takuya
    Tobisu, Mamoru
    ACS CATALYSIS, 2024, 14 (23): : 18216 - 18222
12345