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Yu. V. Shklyaev - One of the best experts on this subject based on the ideXlab platform.
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Spirocyclohexadienones. Part 12. Dienone—Phenol Rearrangement of 1-Substituted 2-Azaspiro[4.5]undeca-1,6,9-trienes and Their Analogues.
ChemInform, 2012Co-Authors: Vladimir A. Glushkov, E. V. Rotermel, T. F. Odegova, Yu. V. ShklyaevAbstract:The hydrolytic cleavage of the spiro compounds in acid media is accompanied by dienone—phenol Rearrangement to furnish substituted N-(hydroxyphenylethyl)-carboxylic amides.
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Spirocyclohexadienones: XII. Dienone-Phenol Rearrangement of 1-substituted 2-azaspiro[4.5]undeca-1,6,9-trienes and their analogs
Russian Journal of Organic Chemistry, 2011Co-Authors: Vladimir A. Glushkov, T. F. Odegova, E. V. Rotermel’, Yu. V. ShklyaevAbstract:Hydrolytic cleavage of 1-substituted 2-azaspiro[4.5]undeca-1,6,9-trienes in acid medium is accompanied by Dienone-Phenole Rearrangement with formation of substituted N -[2-( p -hydroxyphenyl)ethyl] carboxylic acid amides. 1,2-Dimethoxy-3-oxo-15-phenyl-14-azadispiro[5.1.5.2]pentadeca-1,4,14-triene and 2′-R-7a′-methyl-3a′,4′,5′,6′,7′,7a′-hexahydrospiro[cyclohexa[2,5]diene-1,3′-indol]-4-ones undergo analogous cleavage.
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Three-component condensation of methoxyarenes with isobutyraldehyde and α-substituted benzyl cyanides
Russian Journal of Organic Chemistry, 2008Co-Authors: Yu. V. Shklyaev, M. A. El’tsov, O. A. MaiorovaAbstract:Three-component condensation of anisole with isobutyraldehyde and substituted benzyl cyanides gives 1-benzyl-3,3-dimethyl-2-azaspiro[4.5]deca-6,9-dien-8-ones which undergo Dienone-Phenol Rearrangement during the reaction. Analogous condensation of 1-methoxynaphthalene leads to the formation of 2′-benzyl-5′,5′-dimethyl-4′,5′-dihydro-4 H -spiro[naphthalene-1,3′-pyrrol]-4-ones.
Paul-henri Ducrot - One of the best experts on this subject based on the ideXlab platform.
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Baeyer-Villiger reaction of Wieland-Misher ketone derivatives : an alternative to the Dienone-Phenol Rearrangement
Comptes Rendus De L Academie Des Sciences Serie Ii Fascicule C-chimie, 2000Co-Authors: Josiane Beauhaire, Paul-henri DucrotAbstract:Abstract This paper demonstrates the regioselectivity of the Baeyer–Villiger reaction of dicarbonylated compounds such as Wieland–Misher ketone derivatives in favour of oxygen insertion only between the quaternary carbon of the ring junction and the neighbouring carbonyl group. Further reaction sequences allow the formation of various compounds, including phenols and naphtalenones, the later being similar to the result of the Dienone-Phenol Rearrangement of 4-acylcyclohexan-2,5-dienones already described in the literature, as well as 2-carboxy cyclohexenones which might be used as synthons for the synthesis of complex natural products. © 2000 Academie des sciences / Editions scientifiques et medicales Elsevier SAS Wieland–Misher ketone / Baeyer–Villiger / regioselectivity
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Baeyer–Villiger reaction of Wieland–Misher ketone derivatives: an alternative to the dienone–phenol Rearrangement
Comptes Rendus De L Academie Des Sciences Serie Ii Fascicule C-chimie, 2000Co-Authors: Josiane Beauhaire, Paul-henri DucrotAbstract:Abstract This paper demonstrates the regioselectivity of the Baeyer–Villiger reaction of dicarbonylated compounds such as Wieland–Misher ketone derivatives in favour of oxygen insertion only between the quaternary carbon of the ring junction and the neighbouring carbonyl group. Further reaction sequences allow the formation of various compounds, including phenols and naphtalenones, the later being similar to the result of the Dienone-Phenol Rearrangement of 4-acylcyclohexan-2,5-dienones already described in the literature, as well as 2-carboxy cyclohexenones which might be used as synthons for the synthesis of complex natural products. © 2000 Academie des sciences / Editions scientifiques et medicales Elsevier SAS Wieland–Misher ketone / Baeyer–Villiger / regioselectivity
Vladimir A. Glushkov - One of the best experts on this subject based on the ideXlab platform.
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Spirocyclohexadienones. Part 12. Dienone—Phenol Rearrangement of 1-Substituted 2-Azaspiro[4.5]undeca-1,6,9-trienes and Their Analogues.
ChemInform, 2012Co-Authors: Vladimir A. Glushkov, E. V. Rotermel, T. F. Odegova, Yu. V. ShklyaevAbstract:The hydrolytic cleavage of the spiro compounds in acid media is accompanied by dienone—phenol Rearrangement to furnish substituted N-(hydroxyphenylethyl)-carboxylic amides.
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Spirocyclohexadienones: XII. Dienone-Phenol Rearrangement of 1-substituted 2-azaspiro[4.5]undeca-1,6,9-trienes and their analogs
Russian Journal of Organic Chemistry, 2011Co-Authors: Vladimir A. Glushkov, T. F. Odegova, E. V. Rotermel’, Yu. V. ShklyaevAbstract:Hydrolytic cleavage of 1-substituted 2-azaspiro[4.5]undeca-1,6,9-trienes in acid medium is accompanied by Dienone-Phenole Rearrangement with formation of substituted N -[2-( p -hydroxyphenyl)ethyl] carboxylic acid amides. 1,2-Dimethoxy-3-oxo-15-phenyl-14-azadispiro[5.1.5.2]pentadeca-1,4,14-triene and 2′-R-7a′-methyl-3a′,4′,5′,6′,7′,7a′-hexahydrospiro[cyclohexa[2,5]diene-1,3′-indol]-4-ones undergo analogous cleavage.
Josiane Beauhaire - One of the best experts on this subject based on the ideXlab platform.
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Baeyer-Villiger reaction of Wieland-Misher ketone derivatives : an alternative to the Dienone-Phenol Rearrangement
Comptes Rendus De L Academie Des Sciences Serie Ii Fascicule C-chimie, 2000Co-Authors: Josiane Beauhaire, Paul-henri DucrotAbstract:Abstract This paper demonstrates the regioselectivity of the Baeyer–Villiger reaction of dicarbonylated compounds such as Wieland–Misher ketone derivatives in favour of oxygen insertion only between the quaternary carbon of the ring junction and the neighbouring carbonyl group. Further reaction sequences allow the formation of various compounds, including phenols and naphtalenones, the later being similar to the result of the Dienone-Phenol Rearrangement of 4-acylcyclohexan-2,5-dienones already described in the literature, as well as 2-carboxy cyclohexenones which might be used as synthons for the synthesis of complex natural products. © 2000 Academie des sciences / Editions scientifiques et medicales Elsevier SAS Wieland–Misher ketone / Baeyer–Villiger / regioselectivity
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Baeyer–Villiger reaction of Wieland–Misher ketone derivatives: an alternative to the dienone–phenol Rearrangement
Comptes Rendus De L Academie Des Sciences Serie Ii Fascicule C-chimie, 2000Co-Authors: Josiane Beauhaire, Paul-henri DucrotAbstract:Abstract This paper demonstrates the regioselectivity of the Baeyer–Villiger reaction of dicarbonylated compounds such as Wieland–Misher ketone derivatives in favour of oxygen insertion only between the quaternary carbon of the ring junction and the neighbouring carbonyl group. Further reaction sequences allow the formation of various compounds, including phenols and naphtalenones, the later being similar to the result of the Dienone-Phenol Rearrangement of 4-acylcyclohexan-2,5-dienones already described in the literature, as well as 2-carboxy cyclohexenones which might be used as synthons for the synthesis of complex natural products. © 2000 Academie des sciences / Editions scientifiques et medicales Elsevier SAS Wieland–Misher ketone / Baeyer–Villiger / regioselectivity
Yasumasa Hamada - One of the best experts on this subject based on the ideXlab platform.
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formal meta specific intramolecular friedel crafts allylic alkylation of phenols through a spirocyclization dienone phenol Rearrangement cascade
ChemInform, 2014Co-Authors: Mariko Yoshida, Tomoyuki Nozaki, Tetsuhiro Nemoto, Yasumasa HamadaAbstract:The Lewis acid catalyzed reaction yields 3,4-disubstituted phenols from dienones in a highly efficient Rearrangement or from allylic substituted phenoles in a cascade reaction.
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Formal meta‐Specific Intramolecular Friedel—Crafts Allylic Alkylation of Phenols Through a Spirocyclization—Dienone—Phenol Rearrangement Cascade.
ChemInform, 2014Co-Authors: Mariko Yoshida, Tomoyuki Nozaki, Tetsuhiro Nemoto, Yasumasa HamadaAbstract:The Lewis acid catalyzed reaction yields 3,4-disubstituted phenols from dienones in a highly efficient Rearrangement or from allylic substituted phenoles in a cascade reaction.
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formal meta specific intramolecular friedel crafts allylic alkylation of phenols through a spirocyclization dienone phenol Rearrangement cascade
Tetrahedron, 2013Co-Authors: Mariko Yoshida, Tomoyuki Nozaki, Tetsuhiro Nemoto, Yasumasa HamadaAbstract:Abstract Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols was achieved based on spirocyclization–dienone–phenol Rearrangement cascades. Systematic screening of acid catalysts revealed that Sc(OTf)3 was a highly effective catalyst for dienone–phenol Rearrangement of spiro[4.5]cyclohexadienones. Using 5 mol % of Sc(OTf)3 as the promoter, various spirocyclic substrates were transformed into the corresponding phenol derivatives in good to excellent yield. Furthermore, the one-pot sequential spirocyclization–dienone–phenol Rearrangement proceeded using a palladium and scandium multi-catalytic system or a triphenylmethyl cation single-catalyst system, providing the corresponding meta-allylated phenol derivatives in excellent yield.
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Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols through a spirocyclization–dienone–phenol Rearrangement cascade
Tetrahedron, 2013Co-Authors: Mariko Yoshida, Tomoyuki Nozaki, Tetsuhiro Nemoto, Yasumasa HamadaAbstract:Abstract Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols was achieved based on spirocyclization–dienone–phenol Rearrangement cascades. Systematic screening of acid catalysts revealed that Sc(OTf)3 was a highly effective catalyst for dienone–phenol Rearrangement of spiro[4.5]cyclohexadienones. Using 5 mol % of Sc(OTf)3 as the promoter, various spirocyclic substrates were transformed into the corresponding phenol derivatives in good to excellent yield. Furthermore, the one-pot sequential spirocyclization–dienone–phenol Rearrangement proceeded using a palladium and scandium multi-catalytic system or a triphenylmethyl cation single-catalyst system, providing the corresponding meta-allylated phenol derivatives in excellent yield.