NHC-Catalyzed [3+3] Cycloaddition of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles

被引:0
|
作者
Cao, Wei [1 ]
Zhang, Kai [1 ]
Yu, Chenxia [1 ]
Yao, Changsheng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
N-heterocyclic carbene; 2-(acetoxymethyl)buta-2,3-dienoate; 4<italic>H</italic>-pyran; PHOSPHINE CATALYSIS; ACETOXY ALLENOATES; ALLENES; ANNULATIONS; BETA';
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diverse transformations of allenoates catalyzed by Lewis bases have emerged as a powerful platform for generating new chemical entities in organic synthesis. Herein, an N-heterocyclic carbene (NHC) catalyzed [3+3] cyclization of 2-(acetoxymethyl)buta-2,3-dienoates with 1 C,3O-bisnucleophiles has been developed. This approach provides a facile method to synthesize highly functionalized 4H-pyran derivatives with a broad substrate scope (31 examples, up to 83 % yield).
引用
收藏
页数:5
相关论文
共 50 条
  • [41] Enantioselective hydrogenation using cinchona-modified Pt/γ-Al2O3 catalysts:: comparison of the reaction of ethyl pyruvate and buta-2,3-dione
    Li, XB
    Dummer, N
    Jenkins, R
    Wells, RPK
    Wells, PB
    Willock, DJ
    Taylor, SH
    Johnston, P
    Hutchings, GJ
    CATALYSIS LETTERS, 2004, 96 (3-4) : 147 - 151
  • [42] Ru(ii)-catalyzed synthesis of indolo[2,3-c]isoquinolines via [3+3] annulation of N,N'-cyclic azomethine ylides and 3-diazoindolin-2-imines
    Valapil, Durgesh Gurukkala
    Mishra, Priyanka
    Jungare, Kalyani
    Shankaraiah, Nagula
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (37) : 17586 - 17591
  • [43] BPh3 catalyzed [2+3] cycloaddition of Ph3P=C=C=O with nitrones to 4-triphenylphosphoranylidene-5-isoxazolidinones
    Brar, Amandeep
    Unruh, Daniel
    Krempner, Clemens
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [44] Pd-Catalyzed C-S Activation for [3+3] Annulation of 2-(Methylthio)benzofuran-3-carboxylates and 2-Hydroxyphenylboronic Acids: Synthesis of Coumestan Derivatives
    Liu, Jingxin
    Liu, Yingjie
    Du, Wenting
    Dung, Ying
    Liu, Jun
    Wang, Mang
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14): : 7293 - 7297
  • [45] Access to Spiropyrazolone-butenolides through NHC-Catalyzed [3+2]-Asymmetric Annulation of 3-Bromoenals and 1H-Pyrazol-4,5-diones
    Gil-Ordonez, Marta
    Maestro, Alicia
    Andres, Jose M.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 6890 - 6900
  • [46] Octa-n-butyl-1κ2C,2κ2C,3κ2,4κ2C-bis(μ-2,3-dibromopropionato)-1:2κ2O:O′,3:4κ2O:O′-bis(2,3-dibromopropionato)-1κO,3κO-di-μ3-oxido-1:2:4κ3O:O:O,2:3:4κ3O:O:O-tetratin(IV)
    Win, Yip Foo
    Teoh, Siang Guan
    Ha, Sie Tiong
    Kia, Reza
    Fun, Hoong-Kun
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M1572 - U869
  • [47] Palladium(O)-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined 2,3-Fused Cyclopentannulated Indoline Derivatives
    Laugeois, Maxime
    Ling, Johanne
    Ferard, Charlene
    Michelet, Veronique
    Ratovelomanana-Vidal, Virginie
    Vitale, Maxime R.
    ORGANIC LETTERS, 2017, 19 (09) : 2266 - 2269
  • [48] Diastereo- and Enantioselective Gold(I)-Catalyzed Intermolecular Tandem Cyclization/[3+3]Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with Nitrones
    Liu, Feng
    Qian, Deyun
    Li, Lei
    Zhao, Xiaoli
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) : 6669 - 6672
  • [49] Total Synthesis of (+)-Tanikolide by a Traceless Stereoinduction Method Using Rhodium(II)-Catalyzed Oxonium Ylide Formation-[2,3]-Sigmatropic Rearrangement and NHC-Catalyzed Ring-Expansion Lactonization
    Nambu, Hisanori
    Jinnouchi, Hikari
    Fujiwara, Tomoya
    Yakura, Takayuki
    SYNLETT, 2016, 27 (07) : 1106 - 1109
  • [50] Rhodium-catalyzed intermolecular [3+3] cycloaddition of vinyl aziridines with C,N-cyclic azomethine imines: stereospecific synthesis of chiral fused tricyclic 1,2,4-hexahydrotriazines
    Zhu, Chao-Ze
    Feng, Jian-Jun
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2017, 53 (34) : 4688 - 4691