Aqueous Iodine(III)-Mediated Stereoselective Oxidative Cyclization for the Synthesis of Functionalized Fused Dihydrofuran Derivatives

被引：61
|
作者：
Ye, Yang [1 ]
Wang, Linfei [1 ]
Fan, Renhua [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai Key Lab Mol Catalysts & Innovat Mat, Shanghai 200433, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTION; C-H BONDS; ORGANIC-REACTIONS; 1,3-DICARBONYL COMPOUNDS; MANGANESE(III) ACETATE; ALPHA-HYDROXYLATION; POLYVALENT IODINE; AMMONIUM-NITRATE; ORGANOHYPERVALENT IODINE; HETEROCYCLIC-COMPOUNDS;
D O I：
10.1021/jo902553k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient aqueous oxidative cyclization mediated by the combination of iodosobenzene with tetra-(n-butyl)-ammonium iodide provides a new convenient and useful route to functionalized fused dihydrofuran derivatives in moderate to excellent yields with high diastereoselectivities.
引用
收藏
页码：1760 / 1763
页数：4
相关论文
共 50 条
  • [31] A short and stereoselective synthesis of functionalized pentenomycin derivatives
    Khan, FA
    Dash, J
    Rout, B
    TETRAHEDRON LETTERS, 2004, 45 (50) : 9285 - 9288
  • [32] Phenyliodine(III) Diacetate Mediated Oxidative Cyclization of 1-Alkenoyl-1-carbamoyl Cycloalkanes: Access to Spiro-Fused Dihydrofuran-3(2H)-ones
    Yuan, Jingwen
    Zhang, Qian
    Yu, Mangfei
    Huang, Peng
    Zhang, Rui
    Dong, Dewen
    ORGANIC LETTERS, 2015, 17 (20) : 5012 - 5015
  • [33] A Stereoselective Oxidative Polycyclization Process Mediated by a Hypervalent Iodine Reagent
    Desjardins, Samuel
    Andrez, Jean-Christophe
    Canesi, Sylvain
    ORGANIC LETTERS, 2011, 13 (13) : 3406 - 3409
  • [34] Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization
    Barluenga, J
    Fañanás, FJ
    Sanz, R
    Fernández, Y
    CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (09) : 2034 - 2046
  • [35] An iodine(III) mediated oxidative rearrangement of enamines: efficient synthesis of α-amino ketones
    Yadagiri, Dongari
    Anbarasan, Pazhamalai
    CHEMICAL COMMUNICATIONS, 2015, 51 (75) : 14203 - 14206
  • [36] A samarium(II)-mediated, stereoselective cyclization for the synthesis of azaspirocycles
    Guazzelli, Giuditta
    Duffy, Lorna A.
    Procter, David J.
    ORGANIC LETTERS, 2008, 10 (19) : 4291 - 4294
  • [37] Highly functionalized dihydrofuran derivatives: Synthesis by diastereoselective intramolecular Wittig reaction
    Azizian, Javad
    Karimi, Ali Reza
    Soleimani, Ebrahim
    Mohammadi, Ali A.
    Mohammadizadeh, Mohammad R.
    HETEROATOM CHEMISTRY, 2006, 17 (04) : 277 - 279
  • [38] Iodine-Mediated Oxidative Dehydrogenation of β-Acylamino Ketones for the Highly Stereoselective Synthesis of (Z)-β-Ketoenamides
    Chang, Hong-Hong
    Hu, Fei
    Gao, Wen-Chao
    Liu, Tao
    Li, Xing
    Wei, Wen-Long
    Qiao, Yan
    SYNLETT, 2016, 27 (10) : 1592 - 1596
  • [39] Synthesis of 2H-Azirines via Iodine-Mediated Oxidative Cyclization of Enamines
    Wang, Manman
    Hou, Jiao
    Yu, Wenquan
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 14954 - 14961
  • [40] Oxidative cyclization of 3-oxopropanenitriles with α,β-unsaturated amides by manganese(III) acetate.: Regio- and stereoselective synthesis of 4-cyano-2,3-dihydrofuran-3-carboxamides
    Burgaz, E. Vildan
    Yilmaz, Mehmet
    Pekel, A. Tarik
    Oektemer, Atilla
    TETRAHEDRON, 2007, 63 (30) : 7229 - 7239
12345