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
  • [1] Total Synthesis of Aspeverin via an Iodine(III)-Mediated Oxidative Cyclization
    Levinson, Adam M.
    ORGANIC LETTERS, 2014, 16 (18) : 4904 - 4907
  • [2] Regioselective synthesis of isoxazoles by hypervalent iodine(III) reagent mediated oxidative cyclization
    Jarvi, Melissa
    Rohde, Greg
    Nemykin, Victor
    Zhdankin, Viktor
    Yoshimura, Akira
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [3] Hypervalent-Iodine(III)-Mediated Oxidative Methodology for the Synthesis of Fused Triazoles
    Kamal, Raj
    Kumar, Vipan
    Kumar, Ravinder
    CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (14) : 1988 - 2000
  • [4] Hypervalent Iodine(III)-Mediated Oxidative Dearomatizing Cyclization of Arylamines
    Jin, Cong-Yang
    Du, Ji-Yuan
    Zeng, Chao
    Zhao, Xian-He
    Cao, Ye-Xing
    Zhang, Xiang-Zhi
    Lu, Xin-Yun
    Fan, Chun-An
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2437 - 2444
  • [5] Modular and stereoselective synthesis of hydroxylated angularly fused tricyclic piperidine derivatives via samarium diiodide mediated cyclization
    Kumaran, Rajendran Senthil
    Bruedgam, Irene
    Reissig, Hans-Ulrich
    SYNLETT, 2008, (07) : 991 - 994
  • [6] Synthesis of ferrocene substituted dihydrofuran derivatives via manganese(III) acetate mediated radical addition-cyclization reactions
    Aslan, Hakan
    Oktemer, Atilla
    Dal, Hakan
    Hokelek, Tuncer
    TETRAHEDRON, 2017, 73 (51) : 7223 - 7232
  • [7] Stereoselective Synthesis of Multifunctional Spirooxindole-Dihydrofuran Derivatives
    Azimi, Razieh
    Baharfar, Robabeh
    Bagheri, Hashem
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (08) : 5272 - 5281
  • [8] Mechanochemical Synthesis of Functionalized Quinolines by Iodine Mediated Oxidative Annulation
    Halder, Atreyee
    Maiti, Debabrata
    De Sarkar, Suman
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (05) : 577 - 580
  • [9] Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization
    Xing, Linlin
    Zhang, Yong
    Du, Yunfei
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (01) : 14 - 37
  • [10] Cyclization of Malonate Derivatives with Iodine(III) Reagents
    Malmedy, Florence
    Wirth, Thomas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (04) : 786 - 789