兵庫県立大学理学研究科物質科学専攻

物質反応論Ⅱ研究室

Organic Chemistry Laboratory

研究業績

Achievemnets

1980-1999 | 2000-2009 | 2010-2019 | 2020-2021

2009

Structural Requirements for Substrate in Highly Enantioselective Hydrogenation over the Cinchonidine-Modified Pd/C. Sugimura, T. et al. J. Catal. 262, 57-64 (2009).
Synthesis of optically active methyl 4-(4-biphenylyl)-3-hydroxybutanoate via enantioselective hydrogenation using tartaric acid-modified nickel catalyst and direct recrystallization. Sugimura, T., Matsuda, T. & Osawa, T. Tetrahedron: Asymmetry 20, 1877-1880 (2009).
Enantioselective Hydrogenation in Water over Chiral Modified Heterogeneous Catalyst Admixed with Organic Solvent. Sugimura, T. & Kim, T. Y. Catal. Lett. 130, 564-567 (2009).
Enantioselective hydrogenation of (E)-a-phenylcinnamic acid over cinchonidine-modified Pd catalysts supported on TiO2 and CeO2. Kubota, T. et al. Catal. Lett. 129, 387-393 (2009).
Conditioning of palladium-on-carbon (Pd/C) for uniform cinchonidine modification to perform highly enantioselective hydrogenation. Kim, T. Y., Yokota, M., Uchida, T. & Sugimura, T. Catal. Lett. 131, 279-284 (2009).
DMEAD: A New Dialkyl Azodicarboxylate for the Mitsunobu Reaction. Hagiya, K., Muramoto, N., Misaki, T. & Sugimura, T. Tetrahedron 65, 6109-6114 (2009).

2008

Stereoselective Insertion of Rhodium Carbenoid to Water under Control with Intramolecular Perticipation of Hydroxy Group. Sugimura, T. & Nagai, T. Chem. Lett. 37, 286-288 (2008).
Heterogeneous Enantioselective Hydrogenation on the Metal Surface Modified by Chiral Molecules, Sugimura, T. in Handbook of Asymmetric Heterogeneous Catalysis (eds K. Ding & Y. Uozumi) 357-382 (Wiley-VCH, 2008).
Unusual Condensation of 3-Thia[5](1,1')ferrocenphane-1,5-dione with Glyoxal. Formation of [1.1](2,3)Tiopheno(1.1')ferrocenophane-1,7-dione. Miyahara, Y., Nishimura, E. & Sugimura, T. J. Org. Chem. 75, 1783-1786 (2008).
Stereoselective Formation of Chiral Ether via Intramolecular O-H Insertion Reaction of a Metal Carbenoid Generated from Diazoacetoacetate. Im, C. Y., Okuyama, T. & Sugimura, T. Euro. J. Org. Chem., 285-294 (2008).
Stereoinduced cyclization of acyloxyalkenes using iodosylbenzene via a 1,3-dioxan-2-yl cation. Fujita, M., Suzawa, H., Sugimura, T. & Okuyama, T. Tetrahedron Lett. 49, 3326-3329 (2008).

2007

Rapid Atropisomerization of 1,1':5',1"-Ternaphthalene-2,2',6',2"-tetrol (TERNOL) and Its Inhibition by Tethering at Positions 7 and 7". Sugimura, T., Matsushita, N., Minokami, K. & Kurita, S. Tetrahedron 63, 1762-1769 (2007).
Stereoselective Hydrogenation of Conjugate Diene Directed by Hydroxy Group and Asymmetric Synthesis of Deoxypolypropionate Units. Sugimura, T., Im, C. Y., Sato, Y. & Okuyama, T. Tetrahedron 63, 4027-4038 (2007).
Di-2-methoxyethyl Azodicarboxylate (DMEAD): An Inexpensive and Separation-friendly Alternative Reagent for the Mitsunobu Reaction. Sugimura, T. & Hagiya, K. Chem. Lett. 36, 566-567 (2007).
Structures and physiological roles of all the integral lipids of bovine heart cytochrome c oxidase. Shinzawa-Itoh, K. et al. EMBOJ 26, 1713-1725 (2007).
Carbanion vs. Carbon Radical in Tandem 1,4-Addition to Two Connected Units of Acrylate or Methacrylate. Nagano, S., Hakim, S. S. M. A. & Sugimura, T. Bull. Chem. Soc. Jpn. 80, 2011-2013 (2007).
Carbenoid Addition to Phenols to Give Cycloheptatrienols. Stereochemical Regulation and Ligand-dependent Switching of Chemoselectivity. Im, C. Y., Okuyama, T. & Sugimura, T. Chem. Lett. 36, 314-315 (2007).
Hagiya, K. & Sugimura, T. patent. 33606JP (2007).
Enantiodifferentiating tethrahydrofuranylation of but-3-enyl carboxylates using optically active hypervalent iodine(III) reagents via 1 1,3-dioxan-2-yl cation intermediate. Fujita, M., Okuno, S., Lee, H. J., Sugimura, T. & Okuyama, T. Tetrahedron Lett. 48, 8691-8694 (2007).
Oxygenation vs iodonio substitution during the reactions of alkenylsilanes with iodosylbenzene: participation of the internal oxy group. Fujita, M., Lee, H. J., Sugimura, T. & Okuyama, T. Chem. Commun., 1139-0041 (2007).

2006

Highly Enantioselective Hydrogenation of a-Alkyl-b-arylpropenoic acids over Cinchonidine-Modified Palladium Catalyst. Sugimura, T., Watanabe, J., Uchida, T., Nitta, Y. & Okuyama, T. Catal. Lett. 112, 27-31 (2006).
Enantiomer-Differentiating Hydrogenation of Methyl 3-Cyclopropyl-2-methyl-3-oxopropanoate over Tartaric Acid-Modified Nickel. Performance of Heterogeneous Catalyst in Dynamic Kinetic Resolution. Sugimura, T., Watanabe, J., Nakagawa, S. & Okuyama, T. J. Mol. Catal. 248, 233-236 (2006).
Regioselective Reaction of 1-Alkylidene-2-oxallyl Cations with Furan: Control of [4+3] Cycloaddition, [3+2] Cycloaddition, and Electrophilic Substitution. Fujita, M., Oshima, M., Okuno, S., Sugimura, T. & Okuyama, T. Org. Lett. 8, 4113-4116 (2006).

2005

Stereocontrolled intramolecular meta-arene-alkene photocycloaddition reactions using chiral tethers. Efficiency of the tether derived from 2,4-pentanediol. Sugimura, T., Yamasaki, A. & Okuyama, T. Tetrahedron: Asymmetry 16, 1573-1575 (2005).
Effect of Substrate Structure on Stereoselectivity in Asymmetric Hydrogenation of Unsaturated Carboxylic Acids over Cinchonidine-Modified Palladium Catalyst. Sugimura, T., Watanabe, J., Okuyama, T. & Nitta, Y. Tetrahedron: Asymmetry 16, 1573-1575 (2005).
Perhydroxylation of Chiral Cycloheptatriene Ring through Stepwise Oxidation Under Regio- and Stereocontrol. Sugimura, T., Kagawa, M., Ohuchi, N., Inoue, A. & Okuyama, T. Chem. Lett. 34, 546-547 (2005).
Preparation of Methoxy-Substituted Optically Active 7-Alkoxycarbonylcycloheptatrienes and Their Acid-Promoted Rearrangements. Sugimura, T., Kagawa, M., Ohuchi, N., Hagiya, K. & Okuyama, T. Bull. Chem. Soc. Jpn. 78, 671-676 (2005).
Activation-Temperature Dependence in Enantioselective Hydrogenation of Unsaturated Carboxylic Acids over Cinchonidine-Modified Pd/C Catalysts. Nitta, Y., Watanabe, J., Okuyama, T. & Sugimura, T. J. Catal. 236, 164-167 (2005).
Stereoselective Intramolecular O-H Insertion of Rhodium Carbenoid Controlled by the 2,4-Pentanediol Tether. Im, C. Y., Okuyama, T. & Sugimura, T. Chem. Lett. 34, 1328-1329 (2005).

2004

Asymmetric synthesis of deoxypolypropionate units via stereoselective hydrogenation of optically active cycloheptatriene. Sugimura, T., Sato, Y., Im, C. Y. & Okuyama, T. Org. Lett. 6, 4439-4442 (2004).
Regioselective Formation of Optically Active Cycloheptatrienes by Chiral Tethered Büchner Reaction. Sugimura, T., Ohuchi, N., Kagawa, M., Hagiya, K. & Okuyama, T. Chem. Lett. 33, 404-405 (2004).
[6+2] Cycloaddition of N-phenyltriazolinedione with cycloheptatriene derivatives mediated and stereodirected by a chiral 3-oxy substituent. Sugimura, T., Im, C. Y. & Okuyama, T. Tetrahedron Lett. 45, 1519-1521 (2004).
Entropy-Driven Asymmetric Synthesis with Chiral Tether. Sugimura, T. Euro. J. Org. Chem., 1185-1192 (2004).
In vitro and in vivo anti-allergic activity of soy sauce. Kobayashi, M. et al. International Journal of Molecular Medicine 14, 879-884 (2004).
Quality of life improvement with soy sauce ingredients, Shoyupolysaccharides, in perennial allergic rhinitis: A double-blind placebo-controlled clinical study. Kobayashi, M. et al. International Journal of Molecular Medicine 14, 885-889 (2004).
Asymmetric Hydrogenation of Furan-containing Ketones over Tartaric Acid-Modified Raney Nickel Catalyst. Haruna, N. et al. Heterocycles, 375-386 (2004).
Asymmetric meta-arene-alkene photocycloaddition controlled by chiral 2,4-pentanediol tether. Hagiya, K., Yamasaki, A., Okuyama, T. & Sugimura, T. Tetrahedron: Asymmetry 15, 1409-1417 (2004).

2003

Asymmetric Synthesis by Vapor Phase Pyrolysis. Sugimura, T., Tei, T. & Okuyama, T. Tetrahedron Lett. 44, 3115-3117 (2003).
Asymmetric Synthesis of gem-Dimethylcyclopropane-fused Compounds through Chemo-, Regio-, and Stereoselective Cyclopropanation and Stereospecific Rearrangement. Sugimura, T., Tei, T. & Okuyama, T. Chem. Lett. 32, 128-129 (2003).
Chiral and flexible 2,4-pentanediol-tethered cyclopropanation of olefins with a carbenoid derived from a diazo ester to construct three stereogenic centers. Sugimura, T. et al. Tetrahedron: Asymmetry 14, 881-890 (2003).
Sugimura, T. in Chiral Reagents for Asymmetric Synthesis Handbook of Reagents for Organic Synthesis (ed Leo A. Paquette) 133-134 (John Wiley, 2003).
Sugimura, T. in Chiral Reagents for Asymmetric Synthesis Handbook of Reagents for Organic Synthesis (ed Leo A. Paquette) 398-399 (John Wiley, 2003).
Sugimura, T. in e-EROS (ed Leo A. Paquette) (Wiley, 2003).

2002

"Chiral Perturbation Factor" Approach Reviles Importance of Entropy Term in Stereocontrol of the 2,4-Pentanediol-Tethered Reaction. Tei, T. et al. J. Org. Chem. 67, 6593-6598 (2002).
Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly; Diprion nipponica. Tai, A. et al. Bull. Chem. Soc. Jpn. 75, 111-121 (2002).
Over 98% Optical Yield Achieved by Heterogeneous Catalysis. Substrate Design and Analysis of Enantio-differentiating Factors of Tartaric Acid-Modified Nickel Hydrogenation. Sugimura, T., Nakagawa, S. & Tai, A. Bull. Chem. Soc. Jpn. 75, 355-363 (2002).
Highly Stereoselective Protonation of the Enolate of a Bicyclic Cycloheptatrienyl Lactone Occurs on the Hindered Face. Sugimura, T., Kim, W. H., Kagawa, M. & Okuyama, T. Org. Lett. 4, 2059-2061 (2002).
Novel Acid-catalyzed Rearrangement of Alkoxycarbonylcycloheptatriene Assisted by Alkoxy Substitution. Sugimura, T., Kagawa, M., Hagiya, K. & Okuyama, T. Chem. Lett., 260-261 (2002).
Preparation of gem-dimethylcyclopropane-fused compounds through sigmatropic rearrangements. On/off -switching of tautomerization of 3,4-homotropilidene by steric hindrance. Futagawa, T., Nishiyama, N., Tai, A., Okuyama, T. & Sugimura, T. Tetrahedron 58, 9279-9287 (2002).
Solvolysis of chiral cyclohexylidenemethyl friflate. Evidence against a primary vinyl cation intermediate. Fujita, M., Yamamoto, A., Sugimura, T. & Okuyama, T. J. Phys. Org. Chem. 15, 550-555 (2002).

2001

Application of Modified Hydroxy-Directed Diastereo-differentiating Simmons-Smith Reaction to Unreactive Conjugated Triene. Stereocontrolled Tandem Cyclopropanation-Cope Rearrangement-Cyclopropanation. Tei, T., Sugimura, T., Katagiri, T., Tai, A. & Okuyama, T. Tetrahedron: Asymmetry 12, 2727-2730 (2001).
Oxy-function Promoted hydroboration of Conjugated Dienes with Controlled Allylic Borane Rearrangement. Sugimura, T. et al. Chem. Commun., 2180-2181 (2001).
Synthesis and properties of Optically Active 1,':5',1":5",1"'-Quaternaphthalene-2,2',6',2",6",2"'-hexol (QUANOL). Sugimura, T. et al. Enantiomer 6, 35-42 (2001).
Entropy-Controlled Asymmetric Synthesis. How Differential Activation Entropy Is Induced in Chiral Tethered Reactions. Sugimura, T. et al. Org. Lett. 3, 37-40 (2001).
Hydroxy Directed Zinc Carbenoid Addition to a Remote Olefin. Analysis and Improvement of 2,4-Pentanediol Tethered Furukawa Cyclopropanation. Sugimura, T. et al. Tetrahedron 57, 7495-7499 (2001).
Solvolysis of Optically Active 4-methylcyclohexylidenemethyl Triflate: Evidence against a Primary Vinyl Cation as an Intermediate. Fujita, M., Yamamoto, A., Sugimura, T. & Okuyama, T. Chem. Lett., 806-807 (2001).
Asymmetric Addition of an Electrophile to Naphthalenes Promoted and Stereo-directed by Alcohol. Fujita, M., Matsushima, H., Sugimura, T., Tai, A. & Okuyama, T. J. Am. Chem. Soc. 123, 2946-2957 (2001).

2000

Tai, A. & Sugimura, T. in Chiral Catalyst Immobilization and Recycling (eds Dirk E. De Vos, Ivo F. J. Vankelecom, & Pierre A. Jacobs) 173-209 (Wiley-VHC, 2000).
Effective Resolution of Chiral 1,1':5',1"-Ternaphthalene-2,2',6',2"-tetrol through Camphorsulfonylation, Recrystallization, and Reductive Desulfonylation. Sugimura, T., Wada, M. & Tai, A. Enantiomer 5, 23-28 (2000).
Temperature-Independent Stereocontrolled [2+2] Cycloaddition. Potential of the 2,4-Pentanediol Tether in Asymmetric Reactions as a Differential Activation Entropy Promoter. Sugimura, T., Tei, T., Mori, A., Okuyama, T. & Tai, A. J. Am. Chem. Soc. 122, 2128-2129 (2000).
Isomerization of Oxygen-substituted Cyclopropanes by Metal Catalysis. Sugimura, T. & Ryu, I. J. Synth. Org. Chem. Jpn. 58, 1100-1107 (2000).
Enantio-Differentiating Hydrogenation of Aromatic b-ketoesters over Tartaric Acid-Modified Raney Nickel. Nakagawa, S., Tai, A., Okuyama, T. & Sugimura, T. Topics in Catal. 13, 187-189 (2000).