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

页码：3692 / 3696

页数：5

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