Synthesis of bicyclic lactones via I2-mediated intramolecular tandem C-C/C-O bond formation

被引：6
|
作者：
Maejima, Saki [1 ]
Osuka, Mai [1 ]
Yamaguchi, Eiji [1 ]
Itoh, Akichika [1 ]
机构：
[1] Gifu Pharmaceut Univ, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan
来源：
TETRAHEDRON | 2018年 / 74卷 / 24期
关键词：
Lactones; Polycyclic compounds; Cyclization; C-C bond formation; Molecular iodine; ASYMMETRIC IODOCARBOCYCLIZATION REACTION; OXIDATIVE RADICAL CYCLIZATIONS; MANGANESE(III) ACETATE; EFFICIENT STRATEGY; MOLECULAR-IODINE; GAMMA-LACTONES; ACID; DERIVATIVES; PRECURSORS; ALKENES;
D O I：
10.1016/j.tet.2018.04.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The iodine/DMAP-mediated intramolecular tandem C-C/C-O bond forming reaction of malonate bearing alkene moiety proceeded to give bicyclic lactones with good diastereoselectivity in good yield. The mechanistic investigation was also discussed on the basis of various control experimental results. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2985 / 2990
页数：6
相关论文
共 50 条
  • [41] Base-Promoted Tandem Cyclization for the Synthesis of Benzonitriles by C-C Bond Construction
    Zhu, Cheng-Zhi
    Wei, Yin
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 808 - 813
  • [42] Synthesis of Benzo[b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis
    Henry, Martyn C.
    Sutherland, Andrew
    ORGANIC LETTERS, 2020, 22 (07) : 2766 - 2770
  • [43] Palladium-Catalyzed intramolecular C-H Activation/C-C Bond Formation: A Straightforward Synthesis of Phenanthridines
    Peng, Jinsong
    Chen, Tonghui
    Chen, Chunxia
    Li, Bin
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) : 9507 - 9513
  • [44] Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: C-C Bond Formation through Bimolecular Reductive Elimination
    Brenzovich, William E., Jr.
    Benitez, Diego
    Lackner, Aaron D.
    Shunatona, Hunter P.
    Tkatchouk, Ekaterina
    Goddard, William A., III
    Toste, F. Dean
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) : 5519 - 5522
  • [45] Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones via C-C and C-O bond cleavage
    Aboonajmi, Jasem
    Panahi, Farhad
    Hosseini, Mina Aali
    Aberi, Mahdi
    Sharghi, Hashem
    RSC ADVANCES, 2022, 12 (32) : 20968 - 20972
  • [46] Silver(I)-Mediated Dual Cleavage of C-C and C-O Bonds in the Reaction of Diarylmethylenecyclopropanes with Tetrahydrofuran: Synthesis of 4-(3-Halobut-3-enyloxy)butyl 2,2,2-Trifluoroacetate Derivatives
    Chen, Gen-Qiang
    Tang, Xiang-Ying
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (01) : 194 - 197
  • [47] Recent Advances in Enantioselective C-C Bond Formation via Organocobalt Species
    Yoshikai, Naohiko
    SYNTHESIS-STUTTGART, 2019, 51 (01): : 135 - 145
  • [48] Iron-Mediated C-C Bond Formation via Reductive Coupling with Carbon Dioxide
    Adamson, Tristan T.
    Kelley, Steven P.
    Bernskoetter, Wesley H.
    ORGANOMETALLICS, 2020, 39 (19) : 3562 - 3571
  • [49] Direct β-Acyloxylation of Enamines via PhIO-Mediated Intermolecular Oxidative C-O Bond Formation and Its Application to the Synthesis of Oxazoles
    Liu, Xin
    Cheng, Ran
    Zhao, Feifei
    Zhang-Negrerie, Daisy
    Du, Yunfei
    Zhao, Kang
    ORGANIC LETTERS, 2012, 14 (21) : 5480 - 5483
  • [50] Ce-catalyzed regioselective synthesis of pyrazoles from 1,2-diols via tandem oxidation and C-C/C-N bond formation
    Pal, Chandan Kumar
    Jena, Ashis Kumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 21 (01) : 59 - 64
12345