- Synthesis of activated cyclopropanes by an MIRC strategy: An enantioselective organocatalytic approach to spirocyclopropanes
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An efficient cyclopropanation, by a Michael-initiated ring-closing (MIRC) reaction of 2-arylidene-1,3-indandiones and 2-arylidene malononitriles, has been developed by using different α-monohalogenated methylene active compounds with triethylamine. The first enantioselective cyclopropanation to spirocyclopropanes derived by the reaction of 2-arylidene-1,3-indandiones and dimethyl bromomalonate with a commercially available α,α-L- diarylprolinol as the organocatalyst and K2CO3 as the additive has been accomplished. The spirocyclopropanes were isolated in high yield and up to 85% ee. Notably, the asymmetric one-pot sequential approach to spirocyclopropanes proved to be a feasible process. A simple triethylamine-promoted domino cyclopropanation of 2-arylidene-1,3-indandiones and 2-arylidenemalononitriles with α-monohalogenated methylene-active compounds has been efficiently developed. Spirocyclopropanes derived from 2-arylidene-1,3-indandiones were synthesized with up to 85% ee by using dimethyl bromomalonate and α,α-L-diarylprolinol/K2CO3 system. Copyright
- Russo, Alessio,Meninno, Sara,Tedesco, Consiglia,Lattanzi, Alessandra
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scheme or table
p. 5096 - 5103
(2011/10/12)
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- Electrocatalytic multicomponent cyclization of aromatic aldehydes, malononitrile, and malonates into 3-substituted 2,2-dicyanocyclopropane-1,1- dicarboxylates
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Electrolysis of aromatic aldehydes, malononitrile and malonates in methanol in an undivided cell in the presence of double-mediator system NaBr-NaOAc afforded 3-substi-tuted 2,2-dicyanocyclopropane-1,1-dicarboxylates in 40-60% yields.
- Vereshchagin,Elinson,Dorofeev,Nikishin
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experimental part
p. 902 - 907
(2010/10/04)
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- Reaction of organozinc reagents formed in reaction of dibromomalonic acid dialkyl esters and zinc, with 2-arylmethylenemalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters
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Organozinc compounds, obtained from dibromomalonic acid dialkyl esters and zinc, react with 2-arylmethylmalonic acid dinitriles and 3-aryl-2-cyanopropenoic acid methyl esters forming 3-aryl-2,2-dicyanocyclopropane-1,1-dicarboxylic acid dialkyl esters and
- Shchepin,Stepanyan,Silaichev,Kodess
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p. 1919 - 1921
(2008/02/08)
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- 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
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Electrolysis of an aldehyde, malononitrile and a malonate in an alcohol in an undivided cell in the presence of sodium acetate-sodium halide as a double mediatory system results in the formation of 3-substituted-2,2-dicyanocyclopropane-1,1-dicarboxylates
- Elinson, Michail N.,Feducovich, Sergey K.,Vereshchagin, Anatolii N.,Gorbunov, Sergey V.,Belyakov, Pavel A.,Nikishin, Gennady I.
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p. 9129 - 9133
(2007/10/03)
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- Electrocatalytic transformation of dialkyl malonates and arylidene- or alkylidenemalononitriles into dialkyl esters of 3-substituted 2,2-dicyanocyclopropane-1,1-dicarboxylic acids
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Electrolysis of alcoholic solutions of dialkyl malonates and arylidene- or alkylidenemalononitriles in the presence of NaBr in an undivided cell gave dialkyl esters of 3-substituted 2,2-dicyanocyclopropane-1,1-dicarboxylic acids in 60-90% yields.
- Elinson,Feducovich,Zaimovskaya,Vereshchagin,Gorbunov,Nikishin
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p. 1593 - 1598
(2007/10/03)
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