Double [3+2] cycloaddition of nitrile oxides with allenoates: Synthesis of spirobidihydroisoxazoles

被引:8
|
作者
Sun, Wei [1 ]
Jiang, Feng [1 ]
Liu, Honglei [1 ]
Gao, Xing [1 ]
Jia, Hao [1 ]
Zhang, Cheng [1 ]
Guo, Hongchao [1 ]
机构
[1] China Agr Univ, Dept Appl Chem, Beijing 100193, Peoples R China
基金
中国国家自然科学基金;
关键词
Cycloaddition; Allenoate; Nitrile oxide; Spirocyclic heterocyle; C; N-CYCLIC AZOMETHINE IMINES; BAYLIS-HILLMAN CARBONATES; PHOSPHINE-CATALYZED 3+2; 1,3-DIPOLAR CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; STEREOCONTROLLED SYNTHESIS; DIPOLAR CYCLOADDITIONS; NATURAL-PRODUCTS; ISOXAZOLE RING; ANNULATION;
D O I
10.1016/j.cclet.2018.04.024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The double [3 +2] cycloaddition of allenoates with nitrile oxides is presented. The reaction worked well under mild reaction conditions to give the spirobidihydroisoxazole in moderate to excellent yields with excellent diastereoselectivities. The two dihydroisoxazole rings have been formed via a sequential double [3 + 2] cycloaddition. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:363 / 366
页数:4
相关论文
共 50 条
  • [41] Phosphine-Catalyzed [3+2] Cycloaddition of Aza-Aurones and Allenoates: Enantioselective Synthesis of 2-Spirocyclopentyl-Indolin-3-Ones
    Brambilla, Elisa
    Pozza, Camilla
    Rizzato, Silvia
    Abbiati, Giorgio
    Pirovano, Valentina
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (03)
  • [42] Thermal [3+2] cycloaddition reaction of azomethine imines with allenoates for dinitrogen-fused heterocycles
    Na, Risong
    Liu, Honglei
    Li, Zhen
    Wang, Bo
    Liu, Jun
    Wang, Ming-An
    Wang, Min
    Zhong, Jiangchun
    Guo, Hongchao
    [J]. TETRAHEDRON, 2012, 68 (10) : 2349 - 2356
  • [43] [3+2] Cycloaddition of Nitrile Imines with Enamides: An Approach to Functionalized Pyrazolines and Pyrazoles
    Tu, Liang
    Gao, Limei
    Wang, Xiaomeng
    Shi, Ruijie
    Ma, Rupei
    Li, Junfei
    Lan, Xiaoshuang
    Zheng, Yongsheng
    Liu, Jikai
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 559 - 573
  • [44] An entry to a chiral dihydropyrazole scaffold: Enantioselective [3+2] cycloaddition of nitrile imines
    Sibi, MP
    Stanley, LM
    Jasperse, CP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8276 - 8277
  • [45] Intramolecular [3+2] Cycloaddition Reactions of Unsaturated Nitrile Oxides. A Study from the Perspective of Bond Evolution Theory (BET)
    Adjieufack, Abel Idrice
    Liegeois, Vincent
    Mboumbouo, Ibrahim Ndassa
    Mbadcam, Joseph Ketcha
    Champagne, Benoit
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2018, 122 (37): : 7472 - 7481
  • [46] Reactivity of allenoates toward aziridines: [3+2] and formal [3+2] cycloadditions
    Ribeiro Laia, Fernanda M.
    Pinho e Melo, Teresa M. V. D.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (45) : 6180 - 6182
  • [47] Studies on [2+3] cycloaddition reaction of nitrile oxides to linear dipolarophiles bearing multiple double bonds
    Gucma, Miroslaw
    Golebiewski, W. Marek
    Michalczyk, Alicja Katarzyna
    [J]. MONATSHEFTE FUR CHEMIE, 2016, 147 (10): : 1809 - 1818
  • [48] A Straightforward Access to Trifluoromethylated Spirobipyrazo-lines through a Double (3+2)-Cycloaddition of Fluorinated Nitrile Imines with Alkoxyallenes
    Utecht, Greta
    Mloston, Grzegorz
    Jasinski, Marcin
    [J]. SYNLETT, 2018, 29 (13) : 1753 - 1758
  • [49] STUDIES TOWARD TOTAL SYNTHESIS OF MAYTANSINE BASED ON THE INTRAMOLECULAR NITRILE OXIDE-OLEFIN [3+2] CYCLOADDITION
    KO, SS
    CONFALONE, PN
    STAM, SH
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 139 - ORGN
  • [50] Divergent Phosphine-Catalyzed [2+4] or [3+2] Cycloaddition Reactions of γ-Substituted Allenoates with Oxadienes
    Li, Erqing
    Chang, Meijia
    Liang, Ling
    Huang, You
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (04) : 710 - 714