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
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
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