Chameleon-Like Activating Nature of the Spirooxindole Group in Donor-Acceptor Cyclopropanes

被引：25
|
作者：
Akaev, Audrey A. [1 ]
Melnikov, Mikhail Ya. [1 ]
Budynina, Ekaterina M. [1 ]
机构：
[1] Lomonosov Moscow State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 23期
基金：
俄罗斯基础研究基金会;
关键词：
REACTIVITY; CHEMISTRY; ANIONS; ION;
D O I：
10.1021/acs.orglett.9b04153
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The concept of a chameleon activating group is considered in the context of donor-acceptor cyclopropane chemistry. When spiro-conjugated with cyclopropane, oxindole can act as an acceptor or a donor depending on the electronic nature of vicinal substituents. This dichotomy is reflected in the alteration of chemoselectivity of spiro[oxindole-1,3'-cyclopropane] ring opening with nucleophiles.
引用
收藏
页码：9795 / 9799
页数：5
相关论文
共 50 条
  • [1] Halogenated Donor-Acceptor Cyclopropanes as Donor-Acceptor Cyclopropene Surrogates
    Oliver, Gwyndaf A.
    Kolb, Simon
    George, Malini
    Werz, Daniel B.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [2] Dimerization of donor-acceptor cyclopropanes
    Novikov, Roman A.
    Tomilov, Yury V.
    MENDELEEV COMMUNICATIONS, 2015, 25 (01) : 1 - 10
  • [3] Allylation of donor-acceptor cyclopropanes
    Yu, M
    Pagenkopf, BL
    ORGANIC LETTERS, 2003, 5 (24) : 4639 - 4640
  • [4] The Alkynyl Moiety as a Donor for Donor-Acceptor Cyclopropanes
    Haubenreisser, Stefan
    Hensenne, Peter
    Schroeder, Sebastian
    Niggemann, Meike
    ORGANIC LETTERS, 2013, 15 (09) : 2262 - 2265
  • [5] Carbocycles from donor-acceptor cyclopropanes
    Grover, Huck K.
    Emmett, Michael R.
    Kerr, Michael A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (03) : 655 - 671
  • [6] Cycloadditions of Donor-Acceptor Cyclopropanes and Nitriles
    Pagenkopf, Brian L.
    Vemula, Naresh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2561 - 2567
  • [7] Methods for the synthesis of donor-acceptor cyclopropanes
    Tomilov, Yury V.
    Menchikov, Leonid G.
    Novikov, Roman A.
    Ivanova, Olga A.
    Trushkov, Igor V.
    RUSSIAN CHEMICAL REVIEWS, 2018, 87 (03) : 201 - 250
  • [8] Intramolecular annulations of donor-acceptor cyclopropanes
    Lebold, Terry P.
    Kerr, Michael A.
    PURE AND APPLIED CHEMISTRY, 2010, 82 (09) : 1797 - 1812
  • [9] Donor-Acceptor Cyclopropanes in the Synthesis of Carbocycles
    Ivanova, Olga A.
    Trushkov, Igor, V
    CHEMICAL RECORD, 2019, 19 (11): : 2189 - 2208
  • [10] Chemistry of Donor-Acceptor Cyclopropanes and Cyclobutanes
    不详
    ISRAEL JOURNAL OF CHEMISTRY, 2016, 56 (6-7) : 367 - 368
12345