SYNTHESIS OF CYCLOPENT-2-ENONES THROUGH STEPWISE [3+2] CYCLOADDITION OF SIMPLE SILYL ENOL ETHERS AND ALK-1-YNES

被引:8
|
作者
YAMAGUCHI, M
SEHATA, M
HAYASHI, A
HIRAMA, M
机构
关键词
D O I
10.1039/c39930001708
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of silyl enol ethers and alk-1-ynes with SnCl4-Bu3N reagent followed by DBU, leads to cyclopent-2-enones, through [3 + 2] cycloaddition reactions; the initial carbon-carbon bond formation is carbometallation of alkynes, and the second step is a base-promoted intramolecular alkylation which reductively eliminates tin species (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).
引用
收藏
页码:1708 / 1709
页数:2
相关论文
共 50 条
  • [31] Direct synthesis of 2-arylazulenes by [8+2] cycloaddition of 2H-cyclohepta[b]furan-2-ones with silyl enol ethers
    Shoji, Taku
    Sugiyama, Shuhei
    Kobayashi, Yoshiaki
    Yamazaki, Akari
    Ariga, Yukino
    Katoh, Ryuzi
    Wakui, Hiroki
    Yasunami, Masafumi
    Ito, Shunji
    CHEMICAL COMMUNICATIONS, 2020, 56 (10) : 1485 - 1488
  • [32] Synthesis and rearrangement of N-organyloxy β-lactams derived from a (4+2)/(3+2) sequential cycloaddition reaction involving enol ethers and nitro alkenes
    van Berkom, LWA
    Kuster, GJT
    de Gelde, R
    Scheeren, HW
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (21) : 4397 - 4404
  • [33] DIRECT SYNTHESIS OF ALKYL 2-ALKYNOATES FROM ALK-1-YNES, CO2, AND BROMOALKANES CATALYZED BY COPPER(I) OR SILVER(I) SALT
    FUKUE, Y
    OI, S
    INOUE, Y
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) : 2091 - 2091
  • [34] Synthesis of functionalized cyclopentenes through catalytic asymmetric [3+2] cycloadditions of allenes with enones
    Wilson, JE
    Fu, GC
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (09) : 1426 - 1429
  • [35] Pyridine and benzyltriethylammonium chloride ate-complexes of 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole in reactions with alk-1-ynes
    Nemtarev, Andrey V.
    Mironov, Vladimir F.
    Varaksina, Elena N.
    Nelyubina, Yulia V.
    Antipin, Mikhail Yu.
    Musin, Rashid Z.
    Konovalov, Alexander I.
    MENDELEEV COMMUNICATIONS, 2007, 17 (06) : 327 - 329
  • [36] Synthesis and aldol reaction of silyl enol ethers utilizing 2,5-dimethyl-1-phenyl-1-silacyclopentane
    Nagao, Y
    Tanaka, N
    Kozawa, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U139 - U139
  • [37] Asymmetric Synthesis of Tetrahydroquinolines through a [3+2] Cycloaddition Controlled by Dienamine Catalysis
    Li, Wenjun
    Wei, Jia
    Jia, Qianfa
    Du, Zhiyun
    Zhang, Kun
    Wang, Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (22) : 6592 - 6596
  • [38] SYNTHESIS OF 1,4-DIKETONES FROM SILYL ENOL ETHERS AND NITROOLEFINS - 2-(2-OXOPROPYL)CYCLOHEXANONE
    MIYASHITA, M
    YANAMI, T
    YOSHIKOSHI, A
    ORGANIC SYNTHESES, 1981, 60 : 117 - 120
  • [39] Synthesis of 2-alkylidenepyrrolidines, pyrroles, and indoles by condensation of silyl enol ethers and 1,3-bis-silyl enol ethers with 1-azido-2,2-dimethoxyethane and subsequent reductive cyclization
    Bellur, E
    Görls, H
    Langer, P
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12): : 4751 - 4761
  • [40] A new regioselective synthesis of 3-substituted furan-2(5H)-ones by palladium-catalysed reductive carbonylation of alk-1-ynes
    Gabriele, B
    Salerno, G
    Costa, M
    Chiusoli, GP
    TETRAHEDRON LETTERS, 1999, 40 (05) : 989 - 990