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From Umpolung to Alternation: Modified Reactivity of Donor-Acceptor Cyclopropanes Towards Nucleophiles in Reaction with Nitroalkanes
被引:45
作者:

Budynina, Ekaterina M.
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Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

Ivanov, Konstantin L.
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Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

Chagarovskiy, Alexey O.
论文数: 0 引用数: 0
h-index: 0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
Fed Res Ctr Pediat Hematol Oncol & Immunol, Lab Chem Synth, Moscow 117997, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

Rybakov, Victor B.
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h-index: 0
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Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

Trushkov, Igor V.
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h-index: 0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
Fed Res Ctr Pediat Hematol Oncol & Immunol, Lab Chem Synth, Moscow 117997, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

Melnikov, Mikhail Ya.
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h-index: 0
机构:
Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
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
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.).
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页码:3692 / 3696
页数:5
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