Research Topics
| Seijiro MatsubaraSummaryAffiliation: Kyoto University Country: Japan Publications
| Collaborators
|
Detail Information
Publications
Palladium-catalyzed decarboxylation and decarbonylation under hydrothermal conditions: decarboxylative deuterationSeijiro Matsubara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
Org Lett 6:2071-3. 2004..Under the hydrothermal conditions of deuterium oxide, decarbonylative deuteration was observed to give fully deuterated hydrocarbons from carboxylic acids or aldehydes...
Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediatesKeisuke Asano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
Org Lett 14:1620-3. 2012..The reaction proceeds via the formation of hemiacetal intermediates between γ-hydroxy-α,β-unsaturated ketones and aldehydes...- Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediatesTakaaki Okamura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
Chem Commun (Camb) 48:5076-8. 2012..This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks... - Silver-catalyzed intramolecular chloroamination of allenes: easy access to functionalized 3-pyrroline and pyrrole derivativesMasahiro Sai
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto Daigaku Katsura, Nishikyo ku, Kyoto 615 8510, Japan
Org Lett 13:4676-9. 2011..The chloroamination products are useful synthetic intermediates and can be easily transformed into functionalized 3-pyrroline and pyrrole derivatives... - Nickel-catalyzed cycloaddition of salicylic acid ketals to alkynes via elimination of ketonesAkihiro Ooguri
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
J Am Chem Soc 131:13194-5. 2009..A mechanistic rationale is proposed, implying beta-elimination of ketone from ring strained seven-membered nickelacycle to generate a five-membered oxa-nickelacycle intermediate... - Nickel-catalyzed cycloaddition of anthranilic acid derivatives to alkynesNobuyoshi Maizuru
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan
Org Lett 13:1206-9. 2011..The reaction involves oxidative addition of Ni(0) to an ester moiety, which allows intermolecular addition to alkynes via decarbonylation and 1,3-acyl migration... - Nickel-catalyzed [4 + 2] cycloaddition of enones with alkynesIchiro Koyama
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
J Am Chem Soc 131:1350-1. 2009..A mechanistic rationale is proposed, implying oxa-nickela cycle formation by oxidative cyclization of nickel to enone, followed by alkyne insertion... - Cobalt(III) porphyrin catalyzed aza-Diels-Alder reactionRyota Wakabayashi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 14:4794-7. 2012..Highly chemoselective cycloaddition of imines with dienes in the presence of a variety of carbonyl compounds was also demonstrated... - A tandem reaction initiated by 1,4-addition of bis(iodozincio)methane for 1,3-diketone formationMutsumi Sada
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
J Am Chem Soc 132:432-3. 2010..The overall reaction gives 1,3-diketones efficiently... - Asymmetric catalytic cycloetherification mediated by bifunctional organocatalystsKeisuke Asano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
J Am Chem Soc 133:16711-3. 2011..This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature... - Nickel-catalyzed decarbonylative addition of anhydrides to alkynesYuichi Kajita
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
J Am Chem Soc 130:17226-7. 2008..A mechanistic rationale is proposed, implying reductive elimination of Ni(0) promoted by ZnCl(2) cocatalyst as the key step of the catalytic cycle... - Nickel-iminophosphine-catalyzed [4+2] cycloaddition of enones with allenes: synthesis of highly substituted dihydropyransSaori Sako
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Chem Commun (Camb) 47:6150-2. 2011..Enones were found to react with allenes intermolecularly in the presence of a catalytic amount of a nickel-iminophosphine complex to provide dihydropyrans via oxidative cyclization of an enone and Ni(0)... - Transition-metal-catalyzed sequential cross-coupling of bis(iodozincio)methane and -ethane with two different organic halidesHideaki Yoshino
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-katsura, Nishikyo, Japan
Chemistry 12:721-6. 2006..Bis(iodozincio)ethane can also undergo this transformation, yielding a new stereogenic center. The asymmetric induction of this stereogenic center was investigated by using a chiral palladium catalyst... - Preparation of enolate-homoenolate species as (Z)-gamma-siloxyallylmetal equivalents: sequential 1,4-addition of bis(iodozincio)methane to 1,4-dicarbonylbutenes and cyclopropanationTakaharu Hirayama
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-Katsura, Nishikyo, Kyoto 615-8501, Japan
Angew Chem Int Ed Engl 44:3293-6. 2005 - Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivativesSeijiro Matsubara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto, Japan
Chirality 15:38-40. 2003.... - Stereospecific and stereoselective preparation of 2-(1-hydroxyalkyl)-1-alkylcyclopropanols from alpha,beta-epoxy ketones and bis(iodozincio)methaneKenichi Nomura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-Katsura, Nishikyo, Kyoto 615-8501, Japan
Angew Chem Int Ed Engl 44:5860-3. 2005 - Preparation and reaction of 2-aryl-3-silyl-1,3-butadieneZenichi Ikeda
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-Katsura, Nishikyo, Japan
Org Lett 7:4859-61. 2005..A subsequent cross-coupling reaction of the product with another aryl halide gave an unsymmetrical 2,3-diaryl-1,3-butadiene efficiently... - Nickel-catalyzed intermolecular codimerization of acrylates and alkynesHiroaki Horie
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan mbox media kyoto u ac jp
Chem Commun (Camb) 47:2658-60. 2011..The linear codimerization of acrylates and alkynes to produce 1,3-dienes is successfully demonstrated using a nickel catalyst in association with 2-aminopyridine as an additive... - Platinum(IV) oxide catalyzed H-D exchange reactions in arylsilanesMitsuru Yamamoto
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-katsura, Nishikyo, Kyoto 615-8510, Japan
Org Lett 6:5015-7. 2004..Arylsilanols were also labeled with regioselectively under the same conditions... - Methylenecyclopropanes in [4+1] cycloaddition with enonesTasuku Inami
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 13:3837-9. 2011..The reaction outcome is attributed to the transformation of methlenecyclopropane, which is incorporated into a five-membered ring as a one-carbon fragment... - A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocentersMutsumi Sada
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
Org Biomol Chem 9:1389-93. 2011..Thus formed zinc species afforded a cyclohexene derivative via a self-condensation reaction. It is noteworthy that the three adjacent stereogenic centers were created in a single process with quite high diastereoselectivity... - Manganese porphyrin catalyzed cycloisomerization of enynesTakuya Ozawa
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 14:3008-11. 2012..The axial ligand of the catalyst has a marked effect on the product and selectively aids the formation of five- or six-membered cyclic products... - Cationic iron(III) porphyrin-catalyzed [4 + 2] cycloaddition of unactivated aldehydes with simple dienesKyohei Fujiwara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan
J Am Chem Soc 134:5512-5. 2012..Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene... - Nickel-catalyzed [4+2] cycloaddition for highly substituted arenesHiroaki Horie
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Chem Commun (Camb) 48:3866-8. 2012..This formal inverse electron-demand Diels-Alder cycloaddition is attributed to the formation of a seven-membered nickelacycle from a diene and an alkyne... - Dehydrogenative Diels-Alder reactionTakuya Ozawa
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 13:5390-3. 2011..It was found that a key requirement of this process is the presence of a silyl group attached to the alkyne moiety, which forces a dehydrogenation reaction to occur... - Nickel-catalyzed cycloadditions of thiophthalic anhydrides with alkynesTasuku Inami
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 13:1912-5. 2011..Selective formations of thioisocoumarins, benzothiophenes, and thiochromones were accomplished with three different reaction conditions... - Nucleophilic Cyclopropanation Reaction with Bis(iodozincio)methane by 1,4-Addition to alpha,beta-Unsaturated Carbonyl CompoundsKenichi Nomura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510 Japan, Fax 81 75 383 2463
Chem Asian J 4:1298-303. 2009..Additionally, reaction of the obtained homoenolate equivalents with imines give 1-(E)-alkenyl-2-(1-aminoalkyl)alkanols diastereoselectively... - Nickel-catalyzed cycloaddition of o-arylcarboxybenzonitriles and alkynes via cleavage of two carbon-carbon σ bondsKenichiro Nakai
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
J Am Chem Soc 133:11066-8. 2011..The reaction process displays an unusual mechanistic feature-the cleavage of two independent C-CN and C-CO bonds... - Selective synthesis of trienes and dienes via nickel-catalyzed intermolecular cotrimerization of acrylates and alkynesHiroaki Horie
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Chem Commun (Camb) 46:7229-31. 2010..Tailoring nickel-catalyzed linear cotrimerization of acrylates and alkynes effectively proceeds to produce trienes and dienes highly selectively... - Methylenecyclopropane as C1 synthetic units: [1+4] cycloaddition via a nickel catalystTasuku Inami
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Chem Commun (Camb) 47:9711-3. 2011..The reactions represent a new use for methylenecyclopropane as a possible one-carbon building block to replace carbon monoxide, isocyanides, and Fischer carbene complexes... - Dynamic motion of building blocks in porous coordination polymersSatoshi Horike
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Angew Chem Int Ed Engl 45:7226-30. 2006 - Stereospecific Construction of Chiral Tertiary and Quaternary Carbon by Nucleophilic Cyclopropanation with Bis(iodozincio)methaneKenichi Nomura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510 Japan, Fax 81 75 383 2463
Chem Asian J 5:147-52. 2010..When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active alpha-tertiary or -quaternary ketone that retains high optical purity... - Nickel-catalyzed decarboxylative carboamination of alkynes with isatoic anhydridesYasufumi Yoshino
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
J Am Chem Soc 131:7494-5. 2009..A mechanistic rationale is proposed, implying oxidative addition of Ni(0) to a carbamate, which allows intermolecular addition to alkynes via decarboxylation... - Decarbonylative cycloaddition of phthalic anhydrides with allenesYosuke Ochi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 13:1374-7. 2011..The asymmetric variant of the cycloaddition was also achieved by using chiral phosphine ligands to provide δ-lactones enantioselectively... - Preparation of a cycloheptane ring from a 1,2-diketone with high stereoselectivityYoshiaki Takada
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
Org Lett 12:5204-5. 2010..Bis(iodozincio)methane converted the diketone into the cis-divinylcyclopropane-1,2-diol stereoselectively; this diol transformed into the corresponding cycloheptane derivative stereospecifically via Cope rearrangement... - A new zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1-alkylcyclopropanolKenichi Nomura
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510, Japan
Chemistry 16:703-8. 2010..When bicyclo[13.1.0]pentadecane-1,15-diol was treated with the organozinc ate complex, the corresponding 14-membered cyclic vic-diol was obtained. Thus, this rearrangement is also useful for changing the ring size of cyclic substrates... - Decarbonylative cycloaddition of phthalimides with 1,3-dienesKyohei Fujiwara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Org Lett 12:4548-51. 2010..The decarbonylative cycloadditions of phthalimides with 1,3-dienes were performed by using nickel catalyst. The reactions afford 3-vinyldihydroisoquinolones regioselectively with respect to both 1,3-dienes and phthalimides... - 1,4-Addition of bis(iodozincio)methane to α,β-unsaturated ketones: chemical and theoretical/computational studiesMutsumi Sada
Department of Material Chemistry, Graduate School of Engineering, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
Chemistry 16:10474-81. 2010..A theoretical/computational study indicates that the whole reaction pathway is exothermic, and that two zinc atoms of bis(iodozincio)methane accelerate each step cooperatively as effective Lewis acids... - Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanatesTakuya Ozawa
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
Chem Commun (Camb) 46:8055-7. 2010..Intermolecular [2+2+1] cycloaddition which incorporates an alkyne, an isocyanate, and an alkene into a γ-butyrolactam proceeds with nickel catalyst...