Nucleophilic ring opening of imidazolone activated donor-acceptor cyclopropanes with alcohols

被引：5
|
作者：
Ikonnikova, Viktoria A. [1 ,2 ]
Zhigileva, Ekaterina A. [1 ,3 ]
Kuleshov, Andrei, V [1 ,3 ]
Shirokova, Vasilissa V. [1 ,2 ]
Baranov, Mikhail S. [1 ]
Mikhaylov, Andrey A. [1 ]
机构：
[1] Russian Acad Sci, MM Shemyakin Yu A Ovchinnikov Inst Bioorgan Chem, Moscow 117997, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Russian Acad Sci, Moscow 125047, Russia
[3] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
来源：
MENDELEEV COMMUNICATIONS | 2021年 / 31卷 / 05期
基金：
俄罗斯科学基金会;
关键词：
donor-acceptor cyclopropanes; spirocyclic compounds; imidazolones; alcohols; nucleophilic ring opening; DERIVATIVES; ACID;
D O I：
10.1016/j.mencom.2021.09.021
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Imidazolone-activated donor-acceptor cyclopropanes undergo alcohol-assisted ring opening under the co-action of p-toluenesulfonic acid. Under the optimized conditions, cyclopropanes and alcohols are coupled in 1,3-fashion with the retention of heterocyclic fragment. Substrates with aromatic donor groups provide the addition products in 75-99% yields as mixtures of two diastereomers.
引用
收藏
页码：657 / 658
页数：2
相关论文
共 50 条
  • [1] Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes Catalyzed by a Bronsted Acid in Hexafluoroisopropanol
    Richmond, Edward
    Vukovic, Vuk D.
    Moran, Joseph
    ORGANIC LETTERS, 2018, 20 (03) : 574 - 577
  • [2] Asymmetric Ring-Opening Reactions of Donor-Acceptor Cyclopropanes and Cyclobutanes
    Wang, Lijia
    Tang, Yong
    ISRAEL JOURNAL OF CHEMISTRY, 2016, 56 (6-7) : 463 - 475
  • [3] Ring Opening of Donor-Acceptor Cyclopropanes with N-Nucle-ophiles
    Budynina, Ekaterina M.
    Ivanov, Konstantin L.
    Sorokin, Ivan D.
    Melnikov, Mikhail Ya.
    SYNTHESIS-STUTTGART, 2017, 49 (14): : 3035 - 3068
  • [4] Ring Opening of Donor-Acceptor Cyclopropanes with Cyanide Ion and Its Surrogates
    Boichenko, Maksim A.
    Andreev, Ivan A.
    Chagarovskiy, Alexey O.
    Levina, Irma I.
    Zhokhov, Sergey S.
    Trushkov, Igor V.
    Ivanova, Olga A.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 1146 - 1157
  • [5] Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor-Acceptor Cyclopropanes
    Wenz, Donald R.
    de Alaniz, Javier Read
    ORGANIC LETTERS, 2013, 15 (13) : 3250 - 3253
  • [6] Ring-opening polymerization of donor-acceptor cyclopropanes catalyzed by Lewis acids
    Hayakawa, Kosuke
    Matsuoka, Shin-ichi
    Suzuki, Masato
    POLYMER CHEMISTRY, 2017, 8 (25) : 3841 - 3847
  • [7] Imidazolone-activated donor-acceptor cyclopropanes with a peripheral stereocenter. A study on stereoselectivity of cycloaddition with aldehydes
    Andrey А. Mikhaylov
    Pavel N. Solyev
    Andrei V. Kuleshov
    Vadim S. Kublitskii
    Aleksander А. Korlyukov
    Vladislav А. Lushpa
    Mikhail S. Baranov
    Chemistry of Heterocyclic Compounds, 2020, 56 : 1092 - 1096
  • [8] Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes with the Cyanate Ion: Access to Spiro[pyrrolidone-3,3'-oxindoles]
    Zaytsev, Sergey V.
    Ivanov, Konstantin L.
    Skvortsov, Dmitry A.
    Bezzubov, Stanislav I.
    Melnikov, Mikhail Ya.
    Budynina, Ekaterina M.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15): : 8695 - 8709
  • [9] Imidazolone-activated donor-acceptor cyclopropanes with a peripheral stereocenter. A study on stereoselectivity of cycloaddition with aldehydes
    Mikhaylov, Andrey A.
    Solyev, Pavel N.
    Kuleshov, Andrei V.
    Kublitskii, Vadim S.
    Korlyukov, Aleksander A.
    Lushpa, Vladislav A.
    Baranov, Mikhail S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (08) : 1092 - 1096
  • [10] Ring-opening reactions of cyclopropanes. Part 8. Nitrosation of donor-acceptor cyclopropanes
    Cermola, F
    Di Gioia, L
    Graziano, ML
    Iesce, MR
    JOURNAL OF CHEMICAL RESEARCH, 2005, (10) : 677 - 681
12345