Hidetomo Imase

Tokyo University of Agriculture and Technology

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i-10 index

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Ken Tanaka

Tokyo Institute of Technology

Keiichi Noguchi

Tokyo University of Agriculture and Technology

Masao Hirano

Tokyo University of Agriculture and Technology

Zack Robinson

University of Missouri–St. Louis

Roberto Adamo

Toscana Life Sciences

Calman A. MacLennan

University of Birmingham

Martin Allan

Harvard University

Allan Saul

Toscana Life Sciences

Huili Zhai

Shanxi Agricultural University

Qiying Hu

University of Electronic Science and Technology of China

Cooperative Institutions

Tokyo University of Agriculture and Technology

Novartis (Switzerland)

Novartis (United States)

Tokyo Institute of Technology

The University of Tokyo

Toscana Life Sciences

Tohoku University

Osaka University

Tokyo University of Science

National Institutes of Health

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Au-Catalyzed Cycloisomerization of N-Alkenyl Alkynylamides to 2-Pyridones

Synfacts (2008)

Hidetomo Imase K. Noguchi Makoto Hirano Ken Tanaka

Reported is a Au(I)/PPh3-catalyzed cycloisomerization of N-alkenyl alkynylamides to substituted 2-pyridones in fair to good yields. The starting amides were readily obtained by N-acylation of imines with alkynoyl chlorides. A cationic Au(I)/PPh3 complex gave the highest conversion while the use of a neutral Au(I)/PPh3 complex was catalytically inactive. The reaction appears to proceed through an endo-dig cyclization mode. Although little versatility in substitution patterns was achieved, 5,6-cyclofused 2-pyridones were obtained in high yields.

Cycloisomerization

Cationic polymerization

10.1055/s-0028-1087459

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Citations (0)

Rh-Catalyzed [2+2+2] Cycloaddition of 1,6-Diynes

Synfacts (2008)

Kenta Tanaka M. Takahashi Hidetomo Imase Toshimasa Osaka Kohki Noguchi

In previous studies, Shibata and others have described asymmetric Rh(I)-catalyzed [2+2+2] cycloadditions of 1,6-diynes with monoalkenes containing an alkoxycarbonyl functionality (J. Am. Chem. Soc. 2006, 128, 13686). In the present work, the authors utilize a Rh(I)/BINAP complex to effect the cycloaddition of various 1,6-diynes with a protected dehydroamino acid. Strong bidentate coordination through the alkene and amide carbonyl moieties with rhodium should provide a tight chelate, leading to high levels of asymmetric induction.

Alkene

Amide

BINAP

10.1055/s-2008-1078001

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Enantioselective synthesis of α,α-disubstituted α-amino acids by Rh-catalyzed [2+2+2] cycloaddition of 1,6-diynes with protected dehydroamino acid

Tetrahedron (2008)

Ken Tanaka Maho Takahashi Hidetomo Imase Takuya Osaka Keiichi Noguchi

Cationic polymerization

BINAP

10.1016/j.tet.2008.04.107

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Citations (31)

ChemInform Abstract: Convergent and Rapid Assembly of Substituted 2‐Pyridones Through Formation of N‐Alkenyl Alkynylamides Followed by Gold‐Catalyzed Cycloisomerization.

ChemInform (2008)

Hidetomo Imase Keiichi Noguchi Masao Hirano Ken Tanaka

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 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.

Cycloisomerization

10.1002/chin.200852148

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Citations (0)

Sugar–Protein Connectivity Impacts on the Immunogenicity of Site‐Selective Salmonella O‐Antigen Glycoconjugate Vaccines

Angewandte Chemie (2015)

Giuseppe Stefanetti Qiying Hu Aimee Usera Zack Robinson Martin Allan

Abstract A series of glycoconjugates with defined connectivity were synthesized to investigate the impact of coupling Salmonella typhimurium O‐antigen to different amino acids of CRM 197 protein carrier. In particular, two novel methods for site‐selective glycan conjugation were developed to obtain conjugates with single attachment site on the protein, based on chemical modification of a disulfide bond and pH‐controlled transglutaminase‐catalyzed modification of lysine, respectively. Importantly, conjugation at the C186‐201 bond resulted in significantly higher anti O‐antigen bactericidal antibody titers than coupling to K37/39, and in comparable titers to conjugates bearing a larger number of saccharides. This study demonstrates that the conjugation site plays a role in determining the immunogenicity in mice and one single attachment point may be sufficient to induce high levels of bactericidal antibodies.

Glycoconjugate

Conjugate

10.1002/ange.201506112

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Citations (9)

ChemInform Abstract: A New Route to Tricyclic 2‐Pyridone Frameworks via Formation of Bicyclic N‐Alkenyl Alkynylamides Followed by Gold‐Catalyzed Cycloisomerization.

ChemInform (2010)

Hidetomo Imase Ken Tanaka

Abstract 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.

Cycloisomerization

Tricyclic

10.1002/chin.201020124

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A New Route to Tricyclic 2-Pyridone Frameworks via Formation of BicyclicN-Alkenyl Alkynylamides Followed by Gold-catalyzed Cycloisomerization

Chemistry Letters (2009)

Hidetomo Imase Ken Tanaka

Abstract A cationic gold(I)/PPh3 complex catalyzes cycloisomerizations of bicyclic N-alkenyl alkynylamides leading to tricyclic 2-pyridone derivatives at room temperature in good yields. The bicyclic N-alkenyl alkynylamides are readily prepared starting from commercially available 2-substituted cycloalkanones.

Cycloisomerization

Tricyclic

Cationic polymerization

10.1246/cl.2009.1152

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Citations (15)

CCDC 692640: Experimental Crystal Structure Determination

The Cambridge Structural Database (2008)

K. Tanaka M. Takahashi Hidetomo Imase T. Osaka K. Noguchi

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccr7r7y

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Citations (0)

Frontispiece: Sugar–Protein Connectivity Impacts on the Immunogenicity of Site‐Selective Salmonella O‐Antigen Glycoconjugate Vaccines

Angewandte Chemie International Edition (2015)

Giuseppe Stefanetti Qiying Hu Aimee Usera Zack Robinson Martin Allan

Glycoproteins In their Communication on page 13198 ff., Q.-Y. Hu, F. Micoli et al. present two methods for the preparation of glycoconjugate vaccines with one single sugar chain linked to one or two positions of a carrier protein.

Glycoconjugate

10.1002/anie.201584561

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Highly Enantioselective Construction of Axial Chirality by Palladium-Catalyzed Cycloisomerization of N-Alkenyl Arylethynylamides

Organic Letters (2009)

Hidetomo Imase Takeshi Suda Yu Shibata Keiichi Noguchi Masao Hirano

A cationic palladium(II)/(S)-xyl-Segphos complex catalyzes enantioselective cycloisomerizations of N-alkenyl arylethynylamides leading to axially chiral 4-aryl-2-pyridones in high yields with high ee values. The present catalysis represents the first enantioselective construction of axial chirality by the transition-metal-catalyzed cycloisomerization.

Cycloisomerization

Cationic polymerization

Axial Chirality

Chirality

10.1021/ol900373z

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Citations (51)