From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes

被引：45
作者：
Budynina, Ekaterina M. [1 ]
Ivanov, Konstantin L. [1 ]
Chagarovskiy, Alexey O. [1 ,2 ]
Rybakov, Victor B. [1 ]
Trushkov, Igor V. [1 ,2 ]
Melnikov, Mikhail Ya. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
[2] Fed Res Ctr Pediat Hematol Oncol & Immunol, Lab Chem Synth, Moscow 117997, Russia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 11期
基金：
俄罗斯科学基金会;
关键词：
heterocyclic compounds; nitro compounds; nucleophilic addition; pyrrolidones; small rings; 3+2 CROSS-CYCLOADDITIONS; D-A CYCLOPROPANES; EFFICIENT STRATEGY; LEWIS; CONSTRUCTION; 1,1-DIESTERS; CYCLIZATION; ANNULATION; CARBONYLS; ACCESS;
D O I：
10.1002/chem.201504593
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A conceptually new type of donor-acceptor cyclopropane reactivity towards nucleophiles has been disclosed. An essential characteristic of the process is an unusual nucleophilic attack on the C(3)-position of a cyclopropane, combined with typical small ring-opening by cleavage of the C(1)-C(2) bond between the acceptor and the donor. Based on this new reaction between cyclopropane-1,1-diesters and nitroalkanes, we developed a convenient approach to -nitroesters that can be efficiently transformed to the substituted pyrrolidones, structural analogues of racetame family drugs (rolipram, phenylpiracetam, etc.).
引用
收藏
页码：3692 / 3696
页数：5
相关论文
共 82 条
  • [1] Alper P. B., 1999, ANGEW CHEM, V111, P3379
  • [2] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
  • [3] 2-5
  • [4] Diastereoselective 1,3-Dipolar Cycloaddition of Nitrones to Donor-Acceptor Cyclopropanes Catalyzed by a Calcium(II) Complex
    Braun, Caroline M.
    Congdon, Elizabeth A.
    Nolin, Kristine A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) : 1979 - 1984
  • [5] Structure-activity relationships of a novel class of Src SH2 inhibitors
    Buchanan, JL
    Vu, CB
    Merry, TJ
    Corpuz, EG
    Pradeepan, SG
    Mani, UN
    Yang, M
    Plake, HR
    Varkhedkar, VM
    Lynch, BA
    MacNeil, IA
    Loiacono, KA
    Tiong, CL
    Holt, DA
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (16) : 2359 - 2364
  • [6] Heterocycles from cyclopropanes: applications in natural product synthesis
    Carson, Cheryl A.
    Kerr, Michael A.
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) : 3051 - 3060
  • [7] Intramolecular donor-acceptor cyclopropane ring-opening cyclizations
    Cavitt, Marchello A.
    Phun, Lien H.
    France, Stefan
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) : 804 - 818
  • [8] [3+2] Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung
    Chagarovskiy, Alexey O.
    Ivanova, Olga A.
    Budynina, Ekaterina M.
    Trushkov, Igor V.
    Melnikov, Mikhail Ya
    [J]. TETRAHEDRON LETTERS, 2011, 52 (34) : 4421 - 4425
  • [9] Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates
    Chagarovskiy, Alexey O.
    Ivanova, Olga A.
    Rakhmankulov, Eduard R.
    Budynina, Ekaterina M.
    Trushkov, Igor V.
    Melnikov, Mikhail Ya.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3179 - 3184
  • [10] Chakrabarty S., 2014, Angew. Chem, V126, P6074, DOI DOI 10.1021/JA4042127
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