Thermal intramolecular [2+2] cycloaddition of allenenes and allenynes: Diastereoselective access to bicyclic nitrogen heterocycles

被引：77
作者：
Ohno, H [1 ]
Mizutani, T
Kadoh, Y
Miyamura, K
Tanaka, T
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
[2] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 32期
关键词：
allenes; bicyclic compounds; cycloaddition; nitrogen heterocycles; regioselectivity;
D O I：
10.1002/anie.200501413
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Squaring the circle: A route to bicyclo-[4.2.0]octane derivatives has been developed by the [2+2] cycloaddition of allenenes or allenynes. The thermal intramolecular [2+2] cycloaddition of simple allenes 1 with an additional multiple bond leads to direct and regioselective formation of the distal adducts 2 in good to excellent yields. (Chemical Equation Presented) © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：5113 / 5115
页数：3
相关论文
共 50 条
  • [21] Preparation, structure, and unique thermal [2+2], [4+2], and [3+2] cycloaddition reactions of 4-vinylideneoxazolidin-2-one
    Horino, Y
    Kimura, M
    Tanaka, S
    Okajima, T
    Tamaru, Y
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (11) : 2419 - 2438
  • [22] Photocatalytic intermolecular [2+2] cycloaddition/dearomatization of indoles: easy access to cyclobutane-fused indolines
    Han, Zeng
    Wang, Lianhui
    Luo, Yuanqi
    Cui, Xiuling
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [23] Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
    de Souza, Wanderson C.
    Matsuo, Bianca T.
    Matos, Priscilla M.
    Correia, Jose Tiago M.
    Santos, Marilia S.
    Koenig, Burkhard
    Paixao, Marcio W.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (11) : 3722 - 3728
  • [24] Regio-divergent nickel catalysis: intramolecular [4+2] and [2+2] cycloaddition reactions between vinylallenes and alkynes
    Arai, Shigeru
    Inagaki, Saki
    Nakajima, Masaya
    Nishida, Atsushi
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (85) : 11268 - 11271
  • [25] New applications of the imine-ketenimine intramolecular [2+2] cycloaddition reaction:: Highly stereocontrolled synthesis of azeto[1,2-a]pyrimidines
    Alajarín, M
    Vidal, A
    Orenes, RA
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (24) : 4222 - 4227
  • [26] Regio- and Diastereoselective Formal [2+2] Cycloaddition of Allenes with Amino-Functionalized Alkenes by Rare-Earth-Catalyzed C(sp2)-H Activation
    Xu, Wenxuan
    Cong, Xuefeng
    An, Kun
    Lou, Shao-Jie
    Li, Zhenghua
    Nishiura, Masayoshi
    Murahashi, Tetsuro
    Hou, Zhaomin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (45)
  • [27] Cycloaddition Reactions of in situ Generated C2D2 in Dioxane: Efficient Synthetic Approach to D2-Labeled Nitrogen Heterocycles
    Voronin, Vladimir V.
    Ledovskaya, Maria S.
    Rodygin, Konstantin S.
    Ananikov, Valentine P.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (41) : 5640 - 5648
  • [28] Nonmetathesis Heterocycle Formation by Ruthenium-Catalyzed Intramolecular [2+2] Cycloaddition of Allenamide-enes to Azabicyclo[3.1.1]heptanes
    Nada, Tomomi
    Yoneshige, Yusuke
    Ii, Yasuhiro
    Matsumoto, Takashi
    Fujioka, Hiromichi
    Shuto, Satoshi
    Arisawa, Mitsuhiro
    [J]. ACS CATALYSIS, 2016, 6 (05): : 3168 - 3171
  • [29] Synthesis of strigolactones analogues by intramolecular [2+2] cycloaddition of ketene-iminium salts to olefins and their activity on Orobanche cumana seeds
    lachia, MathilDe
    Wolf, Hanno Christian
    De Mesmaeker, Alain
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (09) : 2123 - 2128
  • [30] Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized Cyclobuta[a]naphthalen-4-ols
    Liu, Feng
    Wang, Jia-Yin
    Zhou, Peng
    Li, Guigen
    Hao, Wen-Juan
    Tu, Shu-Jiang
    Jiang, Bo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15570 - 15574
12345