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Papers by issaku yamada

Research paper thumbnail of Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous materials expecting diesel-auto emission regulation

Catalysis Today, 2006

Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous m... more Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous materials, which does not rely on the conventional NOx-absorption–reduction-catalysts, is presented for the purpose of de-NOx of diesel-auto emissions. The established catalysts basically consist of mesoporous silica or metal-substituted mesoporous silicates for supports and platinum for active species, which is operated under lean- and rich-conditions. The new catalysts are very active at 150–200 °C and free from difficult problems of SOx-deactivation and hydrothermal ageing of the NOx-absorption–reduction catalyst.

Research paper thumbnail of Asymmetric hydrogenation of acrylic acid derivatives by novel chiral rhodium–phosphinediamine complex catalysts by selective ligation between two amino units of the ligand and electrostatic interaction

Journal of The Chemical Society-perkin Transactions 1, 1997

Research paper thumbnail of A novel chiral phosphinediamine ligand and asymmetric hydrogenation of acrylic acid derivatives

Tetrahedron-asymmetry, 1996

A novel chiral phosphinediamine ligand (PN2) was prepared from (S)-1-phenylethylamine and dichlor... more A novel chiral phosphinediamine ligand (PN2) was prepared from (S)-1-phenylethylamine and dichloroisopropylphosphine. The rhodium-PN2 catalyst utilizing selective ligation of the amino unit and electrostatic interaction between the ligand and a substrate gave high enantioselectivities up to 92% ee in asymmetric hydrogenations of acrylic acid derivatives.Asymmetric reactions utilizing selective ligation of amino unit and the electrostatic interaction between ligand and substrate

Research paper thumbnail of Effective biaryl compound synthesis using cross-coupling reaction with nickel complexes coordinated by diaminophosphine ligands

Journal of Molecular Catalysis A-chemical, 1997

The cross-coupling reaction of aryl halides and aryl Grignard reagents was effectively catalyzed ... more The cross-coupling reaction of aryl halides and aryl Grignard reagents was effectively catalyzed by the diaminophosphine complex catalysts and the reaction was much faster than that catalyzed by aminophosphine complexes and the nickel complexes were more active than palladium complexes. Various biaryl compounds were easily prepared by the reaction with nickel diaminophosphine catalysts.

Research paper thumbnail of Electrostatic interaction and induced fitting of the rhodium(I) complex coordinated by diphosphine ligand having an amino group in the diastereoselective hydrogenation of dehydrodipeptides

Journal of Organometallic Chemistry, 1997

Rhodium(I)-[2-[2-(dimethylamino)ethyl]-1,3-propanediyl]bis(diphenylphosphine) (DPP-AE) catalyst a... more Rhodium(I)-[2-[2-(dimethylamino)ethyl]-1,3-propanediyl]bis(diphenylphosphine) (DPP-AE) catalyst achieved an effective 1,4-asymmetric induction and afforded high diastereoselectivity (max. 96% d.e.) in the hydrogenation of dehydrodipeptides in protic solvents. Activation parameters indicate the important role of the electrostatic interaction for the asymmetric induction in the hydrogenation. Structural study of the rhodium(I) DPP-AE complex by 31P NMR and circular dichroism spectroscopies indicated that induced fitting of the complex occurred by the electrostatic interaction between the ligand (DPP-AE) and dehydrodipeptide to change the dominant skew-conformation of the complex according to the chiral center of the substrate.

Research paper thumbnail of ChemInform Abstract: Asymmetric Transfer Hydrogenation of Benzaldehydes

Cheminform, 2001

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Microencapsulated Catalysts: Catalytic Asymmetric Synthesis Using a Recoverable and Reusable Polymer-Supported Catalyst

Cheminform, 2010

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Asymmetric Transfer Hydrogenation of Benzaldehydes

Organic Letters, 2000

A combined system of RuCl[(R, R)-YCH(C(6)H(5))CH(C(6)H(5))NH(2)](eta(6)-arene) (Y = NSO(2)C(6)H(4... more A combined system of RuCl[(R, R)-YCH(C(6)H(5))CH(C(6)H(5))NH(2)](eta(6)-arene) (Y = NSO(2)C(6)H(4)-4-CH(3) or O) and t-C(4)H(9)OK catalyzes the asymmetric transfer hydrogenation of various benzaldehyde-1-d derivatives with 2-propanol to yield (R)-benzyl-1-d alcohols in 95-99% ee and with >99% isotopic purity. Reaction of benzaldehydes with a DCO(2)D-triethylamine mixture and the R,R catalyst affords the S deuterated alcohols in 97-99% ee.

Research paper thumbnail of CH/π Attraction: The Origin of Enantioselectivity in Transfer Hydrogenation of Aromatic Carbonyl Compounds Catalyzed by Chiralη6-Arene-Ruthenium(II) Complexes

Angewandte Chemie-international Edition, 2001

In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect t... more In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect the stability of stereodetermining transition states (TSs) by exerting electronic influences on metallic centers and also by through-space interactions with the assembled substrates. In our enantioselective asymmetric transfer hydrogenation of aryl alkyl ketones [1±3] or [1-2 H]benzaldehydes by using 2-propanol or formic acid, we intuitively selected Ru II (h 6 -arene) catalysts that possess a chiral 2-amino alcohol or related auxiliary. A theoretical study has now revealed that the enantioselectivity originates not only from the chiral geometry of the fivemembered chelate ring but also from the CH/p attractive interaction [5] between the h 6 -arene ligand and the carbonyl aryl substituent, instead of conventional nonbonded repulsion. This TS stabilization is reminiscent of the origin of endo selectivity in the Diels ± Alder reaction that is based on an attractive secondary interaction between nonreacting sites. A combined system of [RuCl{(R,R)-YCH(C 6 H 5 )CH-(C 6 H 5 )NH 2 }(h 6 -arene)] (Y O or NTs) and an alkaline base in 2-propanol catalyzes transfer hydrogenation of aromatic ketones or aldehydes to give the corresponding R alcohols with fair to excellent enantiomeric purity. [1±4] The real reducing complex is [RuH{(R,R)-YCH(C 6 H 5 )CH(C 6 H 5 )-NH 2 }(h 6 -arene)]. [2c, 7, 8] The general stereochemical outcome [1±4] prompted us to study the TS structures by hybrid density functional theory-based (DFT) calculations. Transfer hydrogenation of carbonyl substrates with 1 occurs by a novel metal ± ligand bifunctional catalysis [1, 2c, 7, 8] (Scheme 1). The hydridic RuÀH and protic NÀH ax in the 18e complex 1 are transferred simultaneously to the CO bond in 2 to form the 16e complex 3 and alcohol 4. The process is reversible. The chiral complex (R,R)-1 reacts with 2 preferentially via ªproximalº TS Si-5 instead of ªdistalº Re-5, giving R-enriched 4. The calculation for the reaction of (R,R)-1 (h 6 -arene C 6 H 6 ) and benzaldehyde at the RMP2/BS-II// B3LYP/LANL2DZ level indicated that 1) the hydrogen

Research paper thumbnail of CH/π Attraction: The Origin of Enantioselectivity in Transfer Hydrogenation of Aromatic Carbonyl Compounds Catalyzed by Chiralη6-Arene-Ruthenium(II) Complexes

Angewandte Chemie, 2001

In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect t... more In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect the stability of stereodetermining transition states (TSs) by exerting electronic influences on metallic centers and also by through-space interactions with the assembled substrates. In our enantioselective asymmetric transfer hydrogenation of aryl alkyl ketones [1±3] or [1-2 H]benzaldehydes by using 2-propanol or formic acid, we intuitively selected Ru II (h 6 -arene) catalysts that possess a chiral 2-amino alcohol or related auxiliary. A theoretical study has now revealed that the enantioselectivity originates not only from the chiral geometry of the fivemembered chelate ring but also from the CH/p attractive interaction [5] between the h 6 -arene ligand and the carbonyl aryl substituent, instead of conventional nonbonded repulsion. This TS stabilization is reminiscent of the origin of endo selectivity in the Diels ± Alder reaction that is based on an attractive secondary interaction between nonreacting sites. A combined system of [RuCl{(R,R)-YCH(C 6 H 5 )CH-(C 6 H 5 )NH 2 }(h 6 -arene)] (Y O or NTs) and an alkaline base in 2-propanol catalyzes transfer hydrogenation of aromatic ketones or aldehydes to give the corresponding R alcohols with fair to excellent enantiomeric purity. [1±4] The real reducing complex is [RuH{(R,R)-YCH(C 6 H 5 )CH(C 6 H 5 )-NH 2 }(h 6 -arene)]. [2c, 7, 8] The general stereochemical outcome [1±4] prompted us to study the TS structures by hybrid density functional theory-based (DFT) calculations. Transfer hydrogenation of carbonyl substrates with 1 occurs by a novel metal ± ligand bifunctional catalysis [1, 2c, 7, 8] (Scheme 1). The hydridic RuÀH and protic NÀH ax in the 18e complex 1 are transferred simultaneously to the CO bond in 2 to form the 16e complex 3 and alcohol 4. The process is reversible. The chiral complex (R,R)-1 reacts with 2 preferentially via ªproximalº TS Si-5 instead of ªdistalº Re-5, giving R-enriched 4. The calculation for the reaction of (R,R)-1 (h 6 -arene C 6 H 6 ) and benzaldehyde at the RMP2/BS-II// B3LYP/LANL2DZ level indicated that 1) the hydrogen

Research paper thumbnail of Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous materials expecting diesel-auto emission regulation

Catalysis Today, 2006

Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous m... more Outstanding low temperature HC-SCR of NOx over platinum-group catalysts supported on mesoporous materials, which does not rely on the conventional NOx-absorption–reduction-catalysts, is presented for the purpose of de-NOx of diesel-auto emissions. The established catalysts basically consist of mesoporous silica or metal-substituted mesoporous silicates for supports and platinum for active species, which is operated under lean- and rich-conditions. The new catalysts are very active at 150–200 °C and free from difficult problems of SOx-deactivation and hydrothermal ageing of the NOx-absorption–reduction catalyst.

Research paper thumbnail of Asymmetric hydrogenation of acrylic acid derivatives by novel chiral rhodium–phosphinediamine complex catalysts by selective ligation between two amino units of the ligand and electrostatic interaction

Journal of The Chemical Society-perkin Transactions 1, 1997

Research paper thumbnail of A novel chiral phosphinediamine ligand and asymmetric hydrogenation of acrylic acid derivatives

Tetrahedron-asymmetry, 1996

A novel chiral phosphinediamine ligand (PN2) was prepared from (S)-1-phenylethylamine and dichlor... more A novel chiral phosphinediamine ligand (PN2) was prepared from (S)-1-phenylethylamine and dichloroisopropylphosphine. The rhodium-PN2 catalyst utilizing selective ligation of the amino unit and electrostatic interaction between the ligand and a substrate gave high enantioselectivities up to 92% ee in asymmetric hydrogenations of acrylic acid derivatives.Asymmetric reactions utilizing selective ligation of amino unit and the electrostatic interaction between ligand and substrate

Research paper thumbnail of Effective biaryl compound synthesis using cross-coupling reaction with nickel complexes coordinated by diaminophosphine ligands

Journal of Molecular Catalysis A-chemical, 1997

The cross-coupling reaction of aryl halides and aryl Grignard reagents was effectively catalyzed ... more The cross-coupling reaction of aryl halides and aryl Grignard reagents was effectively catalyzed by the diaminophosphine complex catalysts and the reaction was much faster than that catalyzed by aminophosphine complexes and the nickel complexes were more active than palladium complexes. Various biaryl compounds were easily prepared by the reaction with nickel diaminophosphine catalysts.

Research paper thumbnail of Electrostatic interaction and induced fitting of the rhodium(I) complex coordinated by diphosphine ligand having an amino group in the diastereoselective hydrogenation of dehydrodipeptides

Journal of Organometallic Chemistry, 1997

Rhodium(I)-[2-[2-(dimethylamino)ethyl]-1,3-propanediyl]bis(diphenylphosphine) (DPP-AE) catalyst a... more Rhodium(I)-[2-[2-(dimethylamino)ethyl]-1,3-propanediyl]bis(diphenylphosphine) (DPP-AE) catalyst achieved an effective 1,4-asymmetric induction and afforded high diastereoselectivity (max. 96% d.e.) in the hydrogenation of dehydrodipeptides in protic solvents. Activation parameters indicate the important role of the electrostatic interaction for the asymmetric induction in the hydrogenation. Structural study of the rhodium(I) DPP-AE complex by 31P NMR and circular dichroism spectroscopies indicated that induced fitting of the complex occurred by the electrostatic interaction between the ligand (DPP-AE) and dehydrodipeptide to change the dominant skew-conformation of the complex according to the chiral center of the substrate.

Research paper thumbnail of ChemInform Abstract: Asymmetric Transfer Hydrogenation of Benzaldehydes

Cheminform, 2001

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of ChemInform Abstract: Microencapsulated Catalysts: Catalytic Asymmetric Synthesis Using a Recoverable and Reusable Polymer-Supported Catalyst

Cheminform, 2010

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Asymmetric Transfer Hydrogenation of Benzaldehydes

Organic Letters, 2000

A combined system of RuCl[(R, R)-YCH(C(6)H(5))CH(C(6)H(5))NH(2)](eta(6)-arene) (Y = NSO(2)C(6)H(4... more A combined system of RuCl[(R, R)-YCH(C(6)H(5))CH(C(6)H(5))NH(2)](eta(6)-arene) (Y = NSO(2)C(6)H(4)-4-CH(3) or O) and t-C(4)H(9)OK catalyzes the asymmetric transfer hydrogenation of various benzaldehyde-1-d derivatives with 2-propanol to yield (R)-benzyl-1-d alcohols in 95-99% ee and with >99% isotopic purity. Reaction of benzaldehydes with a DCO(2)D-triethylamine mixture and the R,R catalyst affords the S deuterated alcohols in 97-99% ee.

Research paper thumbnail of CH/π Attraction: The Origin of Enantioselectivity in Transfer Hydrogenation of Aromatic Carbonyl Compounds Catalyzed by Chiralη6-Arene-Ruthenium(II) Complexes

Angewandte Chemie-international Edition, 2001

In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect t... more In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect the stability of stereodetermining transition states (TSs) by exerting electronic influences on metallic centers and also by through-space interactions with the assembled substrates. In our enantioselective asymmetric transfer hydrogenation of aryl alkyl ketones [1±3] or [1-2 H]benzaldehydes by using 2-propanol or formic acid, we intuitively selected Ru II (h 6 -arene) catalysts that possess a chiral 2-amino alcohol or related auxiliary. A theoretical study has now revealed that the enantioselectivity originates not only from the chiral geometry of the fivemembered chelate ring but also from the CH/p attractive interaction [5] between the h 6 -arene ligand and the carbonyl aryl substituent, instead of conventional nonbonded repulsion. This TS stabilization is reminiscent of the origin of endo selectivity in the Diels ± Alder reaction that is based on an attractive secondary interaction between nonreacting sites. A combined system of [RuCl{(R,R)-YCH(C 6 H 5 )CH-(C 6 H 5 )NH 2 }(h 6 -arene)] (Y O or NTs) and an alkaline base in 2-propanol catalyzes transfer hydrogenation of aromatic ketones or aldehydes to give the corresponding R alcohols with fair to excellent enantiomeric purity. [1±4] The real reducing complex is [RuH{(R,R)-YCH(C 6 H 5 )CH(C 6 H 5 )-NH 2 }(h 6 -arene)]. [2c, 7, 8] The general stereochemical outcome [1±4] prompted us to study the TS structures by hybrid density functional theory-based (DFT) calculations. Transfer hydrogenation of carbonyl substrates with 1 occurs by a novel metal ± ligand bifunctional catalysis [1, 2c, 7, 8] (Scheme 1). The hydridic RuÀH and protic NÀH ax in the 18e complex 1 are transferred simultaneously to the CO bond in 2 to form the 16e complex 3 and alcohol 4. The process is reversible. The chiral complex (R,R)-1 reacts with 2 preferentially via ªproximalº TS Si-5 instead of ªdistalº Re-5, giving R-enriched 4. The calculation for the reaction of (R,R)-1 (h 6 -arene C 6 H 6 ) and benzaldehyde at the RMP2/BS-II// B3LYP/LANL2DZ level indicated that 1) the hydrogen

Research paper thumbnail of CH/π Attraction: The Origin of Enantioselectivity in Transfer Hydrogenation of Aromatic Carbonyl Compounds Catalyzed by Chiralη6-Arene-Ruthenium(II) Complexes

Angewandte Chemie, 2001

In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect t... more In asymmetric catalysis using chiral transition metal complexes, metal ligands generally affect the stability of stereodetermining transition states (TSs) by exerting electronic influences on metallic centers and also by through-space interactions with the assembled substrates. In our enantioselective asymmetric transfer hydrogenation of aryl alkyl ketones [1±3] or [1-2 H]benzaldehydes by using 2-propanol or formic acid, we intuitively selected Ru II (h 6 -arene) catalysts that possess a chiral 2-amino alcohol or related auxiliary. A theoretical study has now revealed that the enantioselectivity originates not only from the chiral geometry of the fivemembered chelate ring but also from the CH/p attractive interaction [5] between the h 6 -arene ligand and the carbonyl aryl substituent, instead of conventional nonbonded repulsion. This TS stabilization is reminiscent of the origin of endo selectivity in the Diels ± Alder reaction that is based on an attractive secondary interaction between nonreacting sites. A combined system of [RuCl{(R,R)-YCH(C 6 H 5 )CH-(C 6 H 5 )NH 2 }(h 6 -arene)] (Y O or NTs) and an alkaline base in 2-propanol catalyzes transfer hydrogenation of aromatic ketones or aldehydes to give the corresponding R alcohols with fair to excellent enantiomeric purity. [1±4] The real reducing complex is [RuH{(R,R)-YCH(C 6 H 5 )CH(C 6 H 5 )-NH 2 }(h 6 -arene)]. [2c, 7, 8] The general stereochemical outcome [1±4] prompted us to study the TS structures by hybrid density functional theory-based (DFT) calculations. Transfer hydrogenation of carbonyl substrates with 1 occurs by a novel metal ± ligand bifunctional catalysis [1, 2c, 7, 8] (Scheme 1). The hydridic RuÀH and protic NÀH ax in the 18e complex 1 are transferred simultaneously to the CO bond in 2 to form the 16e complex 3 and alcohol 4. The process is reversible. The chiral complex (R,R)-1 reacts with 2 preferentially via ªproximalº TS Si-5 instead of ªdistalº Re-5, giving R-enriched 4. The calculation for the reaction of (R,R)-1 (h 6 -arene C 6 H 6 ) and benzaldehyde at the RMP2/BS-II// B3LYP/LANL2DZ level indicated that 1) the hydrogen