Electrocatalytic cascade multicomponent assembling: stereoselective one-pot synthesis of the substituted 3-azabicyclo[3.1.0]hexane-1-carboxylate system from aldehyde, malononitrile, malonate and methanol

被引：45

作者：

Vereshchagin, Anatolii N. ^{[1
]}

Elinson, Michail N. ^{[1
]}

Zaimovskaya, Tatiana A. ^{[2
]}

Nikishin, Gennady I. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

[2] AV Topchiev Petrochem Synth Inst, Moscow 119991, Russia

来源：

TETRAHEDRON | 2008年 / 64卷 / 41期

基金：

俄罗斯基础研究基金会;

关键词：

electrolysis; electrocatalysis; stereoselectivity; cascade transformation; mediators; bicyclic pyrrolidones;

D O I：

10.1016/j.tet.2008.07.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrolysis of aromatic aldehydes, malononitrile and malonate in methanol in an undivided cell in the presence of sodium bromide-sodium methoxide as double mediatory system results in the stereoselective formation of methyl (1R*,5R*,6R*) 6-substituted 5-cyano-4,4-dialkoxy-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylates in 50-70% yields. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：9766 / 9770

页数：5

共 3 条

[1] Electrocatalytic multicomponent cyclization of an aldehyde, malononitrile and a malonate into 3-substituted-2,2-dicyanocyclopropane-1,1-dicarboxylate - the first one-pot synthesis of a cyclopropane ring from three different molecules
Elinson, Michail N.
Feducovich, Sergey K.
Vereshchagin, Anatolii N.
Gorbunov, Sergey V.
Belyakov, Pavel A.
Nikishin, Gennady I.
TETRAHEDRON LETTERS, 2006, 47 (51) : 9129 - 9133
[2] Chemical and electrocatalytic cascade cyclization of Guareschi imides: 'one-pot' simple and efficient way to the 2,4-dioxo-3-azabicyclo[3.1.0]hexane scaffold
Vereshchagin, Anatoly N.
Elinson, Michail N.
Dorofeeva, Evgeniya O.
Demchuk, Dmitry V.
Bushmarinov, Ivan S.
Goloveshkin, Alexander S.
Nikishin, Gennady I.
TETRAHEDRON, 2013, 69 (25) : 5234 - 5241
[3] Stereoselective electrocatalytic transformation of arylidene- or alkylidenemalononitriles and malonate into alkyl (1R,5R,6R)*6-substituted 5-cyano-4,4-dialkoxy-2-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylates
Elinson, MN
Feducovich, SK
Starikova, ZA
Vereshchagin, AN
Gorbunov, SV
Nikishin, GI
TETRAHEDRON LETTERS, 2005, 46 (37) : 6389 - 6393

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