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
  • [11] Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I2-Mediated Oxidative C-O/C-S Bond Formation
    Niu, Pengfei
    Kong, Jinfeng
    Tian, Xianhai
    Song, Lina
    Liu, Hongxu
    Wu, Jie
    Yu, Wenquan
    Chang, Junbiao
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) : 1018 - 1024
  • [12] Construction of Fused Pyrrolidines and β-Lactones by Carbene-Catalyzed C-N, C-C, and C-O Bond Formations
    Wu, Xingxing
    Hao, Lin
    Zhang, Yuexia
    Rakesh, Maiti
    Reddi, Rambabu N.
    Yang, Song
    Song, Bao-An
    Chi, Yonggui Robin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4201 - 4205
  • [13] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [14] Palladium-Mediated Intramolecular C-O and C-C Coupling Reactions: An Efficient Synthesis of Benzannulated Oxazepino- and Pyranocarbazoles
    Prabakaran, Kumaresan
    Zeller, Matthias
    Prasad, Karnam Jayarampillai Rajendra
    SYNLETT, 2011, (13) : 1835 - 1840
  • [15] Iodobenzene-Catalyzed Oxabicyclo[3.2.1]octane and [4.2.1]Nonane Synthesis via Cascade C-O/C-C Formation
    Ngatimin, Marsewi
    Frey, Raphael
    Levens, Alison
    Nakano, Yuji
    Kowalczyk, Marcin
    Konstas, Kristina
    Hutt, Oliver E.
    Lupton, David W.
    ORGANIC LETTERS, 2013, 15 (22) : 5858 - 5861
  • [16] Potassium tert-butoxide mediated C-C, C-N, C-O and C-S bond forming reactions
    Madasu, Jayashree
    Shinde, Shital
    Das, Rudradip
    Patel, Sagarkumar
    Shard, Amit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (41) : 8346 - 8365
  • [17] Palladium(II)-Catalyzed C-H Bond Activation/C-C and C-O Bond Formation Reaction Cascade: Direct Synthesis of Coumestans
    Neog, Kashmiri
    Borah, Ashwini
    Gogoi, Pranjal
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) : 11971 - 11977
  • [18] Tandem Catalysis: Alcohol Oxidation and C-C Bond Formation via C-H Bond Activation
    Simon, Marc-Olivier
    Ung, Gael
    Darses, Sylvain
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (07) : 1045 - 1048
  • [19] A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C-H Bond Activation Followed by C-C and C-O Bond Formation
    Gogoi, Anupal
    Guin, Srimanta
    Rout, Saroj Kumar
    Patel, Bhisma K.
    ORGANIC LETTERS, 2013, 15 (08) : 1802 - 1805
  • [20] Synthesis of Diversely Substituted Indoloquinolinones via Pd(II)/Cu(II)-Mediated Oxidative C-C Bond Formation and I(III)-Mediated C-N Bond Formation
    Zhang, Xiang
    Zhang-Negrerie, Daisy
    Deng, Jun
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24) : 12750 - 12759
12345