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

2021

Effect of methyl-substitution of the quinoline ring of cinchona alkaloides on thr performance as a modifier for the enantioselective hydrogenation of (E)-2,3-di(4-methoxyphenyl)propenoic acid over Pd/C: Kinetic analysis, M. Nakatsuji, T. Kubota, M. Fujita, Y. Okamoto, T. Sugimura, Catal. Lett. 151, 863-874 (2021)

2020

Oxetane Intermediate during a Direct Aldol Reaction: Stereoselective [5+ 1] Annulation Affording Tetralines, T. Kuri, Y. Mizukami, M. Shimogaki, M. Fujita, Org. Lett. 22, 7613–7616 (2020)
Kinetic analysis of the asymmetric hydrogenation of (E)-2,3-diphenylpropenoic acid over cinchonidine derivative-modified Pd/C: , M. Nakatsuji, M. Fujita, Y. Okamoto, T. Sugimura, Catal. Sci. Tech. 10, 6573–6582 (2020)
Kinetic Analysis of Enantioselective Hydrogenation of 2,3-(E)-Diarylpropenoic Acids over a Chiral Cinchona Alkaloid-Modified Pd/C Catalyst, B. Kim, M. Nakatsuji, T. Mameda, T. Kubota, M. Fujita, T. Sugimura and Y. Okamoto, Bull. Chem. Soc. Jpn. 93, 163–175 (2020).

2019

Enhanced enantioselectivity achieved at low hydrogen pressure for the asymmetric hydrogenation of methyl acetoacetate over a tartaric acid NaBr-modified Raney nickel catalyst: a kinetic study, A. A. Choliq, R. Nakae, M. Watanabe, T. Misaki, M. Fujita, Y. Okamoto and T. Sugimura, Bull. Chem. Soc. Jpn. 92, 1175–1180 (2019).
Hydrogen/Deuterium Isotopic Labeling Study of Enantioselective Hydrogenation of (E)-2-Methyl-2-butenoic Acid over a Cinchonidine-modified Pd/C Catalyst, T. Sugimura, S. Tomatsuri, M. Fujita and Y. Okamoto, Bull. Chem. Soc. Jpn. 92, 1737–1742 (2019).

2018

Enantioselective Hydrogenation of Ketones over a Tartaric Acid-Modified Raney Nickel Catalyst: Substrate-Modifier Interaction Strength and Enantioselectivity, A. A. Choliq, E. Murakami, S. Yamamoto, T. Misaki, M. Fujita, Y. Okamoto and T. Sugimura, Bull. Chem. Soc. Jpn. 91, 1325–1332 (2018).
Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III), M. Fujita, K. Miura and T. Sugimura, Beilstein J. Org. Chem. 14, 659–663 (2018).
Enantioselective Heterocycle Formation using Chiral Hypervalent Iodine(III), M. Fujita, Heterocycles 96, 563–594 (2018).
Stereoconvergent 1,4-Addition Reaction of 5H-Oxazol-4-ones with E,Z Isomeric Mixture of Alkylidene β-Ketoesters Catalyzed by Chiral Guanidines,T. Misaki, T. Tatsumi, T. Okamoto, Y. Hayashi, N. Jin and T. Sugimura, Chem. Eur. J. 24, 9778–9782 (2018).

2017

Stereochemical assignment of the unique electron acceptor 5'-hydroxyphylloquinone, a polar analog of vitamin K1 in photosystem I. , M.Kosugi, C.Lee, T.Misaki, M.Fujita and T.Sugimura，Biosci. Biotechnol. Biochem. 81, 2244-2252 (2017).
Stereoselective E/Z-photoisomerization of cyclooctene using 2,4-pentanediol chiral tether, K. Song, M. Fujita, T. Okuyama and T. Sugimura, Tetrahedron: Asymmetry 28, 296-301 (2017).
E/Z-Selectivity Controlled by Participation of Internal Oxy Group During Electrophilic Substitution of Alk-1-enylboronate with Bis(2,4,6-trimethylpyridine)iodonium Salt, M. Fujita, H. J. Lee, C. Ichihara and T. Sugimura, Synthesis 49, 2913-2916 (2017).
Mechanistic Aspects of Alkene Oxidation using Chiral Hypervalent Iodine Reagents, M. Fujita, Tetrahedron Lett. 58, 4409–4419 (2017).
Enantioselective C-C Bond Formation during the Oxidation of 5-Phenylpent-2-enyl Carboxylates with Hypervalent Iodine(III), M. Shimogaki, M. Fujita and T. Sugimura, J. Org. Chem. 82, 11836–11840 (2017).

2016

Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation, M. Shimogaki, M. Fujita and T. Sugimura, Angew. Chem. Int. Ed. 55, 15797-15801 (2016).
Adsorption and Performance of Chiral Cinchona Alkaloid Modifiers over Pd/C Catalyst for Enantioselective Hydrogenation of α-Phenylcinnamic Acids, M. Nakatsuji, T. Misaki, Y. Okamoto and T. Sugimura, Bull. Chem. Soc. Jpn. 89, 1187-1191 (2016).
EXAFS Characterization of Pd Catalysts for Enantioselective Hydrogenation of α-Phenylcinnamic Acid: Pretreatment Effects and Thiol Adsorption, T. Kubota, H. Sato, T. Uchida, T. Y. Kim, K. Omata, T. Misaki, Y. Okamoto and T. Sugimura, Catalysis Lett. 146, 2430-2440 (2016).
Enantioselective Hydrogenation of α-Phenylcinnamic Acids over Cinchonidine-Modified Pd/C Commercial Catalysts, Haruka Sato, Takuya Mameda, Kengo Nakai, Tomonori Misaki, Yuichi Haruyama, Seiji Sonobe, Takeshi Kubota, Yasuaki Okamoto and T. Sugimura, Res. Chem. Intermed. 42, 31-45 (2016).
Enantioselective hydrogenation of b-aryl-b-ketoester over a-hydroxy acid-modified Raney nickel catalysts: competitive hydrogenation with methyl acetoacetate，A. A. Choliq, J. Watanabe, T. Misaki, Y. Okamoto and T. Sugimura, Tetrahedron: Asymmetry 27, 657-662 (2016).

2015

Organocatalytic 1,4-Addition Reaction of 2-Formyl thio esters to Vinylketones: An Efficient Access to Acyclic Chiral Building Blocks with a Quaternary Carbon Stereocenter, T. Tatsumi, T. Misaki and T. Sugimura, Chem. Eur. J. 21, 18971-18974 (2015).
Stereoselective Formation of Substituted 1,3-Dioxolanes through a Three-Component Assembly during the Oxidation of Alkenes with Hypervalent Iodine(III), M. Shimigaki, M. Fujita and T. Sugimura, Molecules 20, 17041-17057 (2015).
1,4-Addition Reaction of 5H-Oxazol-4-ones to Vinyl Ketones Catalyzed by Chiral Guanidines, A. Morita, T. Misaki and T. Sugimura, Tetrahedron Lett. 56, 264-267 (2015).
Highly enantioselective and diastereoselective conjugate addition of 5H-oxazol-4-ones to 2-chloroacrylonitrile catalyzed by chiral guanidines, T. Misaki, N.-R. Choi, A. Morita and T. Sugimura, Tetrahedron Lett. 56, 5063-5066 (2015).
Substrate dependent ligand acceleration in enantioselective hydrogenation of (E)-2,3-diarylpropenoic acid on cinchonidified Pd/C, T. Mameda, K. Nakai, T. Misaki, Y. Okamoto and T. Sugimura, Catalysis Today 245, 129-133 (2015).
Ligand-Acceleration by a Chiral Modifier in the Enantio-selectivitve Hydrogenation of Methyl Acetoacetate on a Raney Nickel Catalyst: Effect of a Modifier Configuration, Sugimura, T., S. Nakagawa, N. Kamata, T. Tei, T. Tajiri, R.-i. Tsukiyama, T. OkuyamaY. Okamotoa, Bull.Chem. Soc. Jpn. 271-276 (2015).
Kinetic and Stereochemical Analyses of Amine-Additive Effects on the Hydrogenation of α-Phenylcinnamic Acid over Cinchonidine-Modified Pd/C, Nakai, K., T. Misaki, Y. OkamotoT. Sugimura, Bull. Chem. Soc. Jpn. 300-302 (2015).
Induction Period for the Enantioselective Hydrogenation of a,b-Unsaturated Acids over a Cinchonidine-Modified Palladium Catalyst, Mameda, T., T. Misaki, Y. OkamotoT. Sugimura, React. Kinet., Mech. Cat. 55-61 (2015).
1,4-Addition reaction of 5H-oxazol-4-ones to vinyl ketones catalyzed by chiral guanidines, A. Morita, T. Misaki and T. Sugimura, Tetrahedron Lett. 56, 264-267 (2015).

2014

A Series of Two Oxidation Reactions of ortho-Alkenylbenzamide with Hypervalent Iodine(III): A Concise Entry into (3R,4R)-4-Hydroxymellein and (3R,4R)-4-Hydroxy-6-methoxymellein, Takesue, T., M. Fujita, T. Sugimura, H. Akutsu, Org Lett. 16, 4634-4637 (2014).
1,6-Addition Reaction of 5H-Oxazol-4-ones to Conjugated Dienones Catalyzed by Chiral Guanidines, A. Morita, T. Misaki and T. Sugmura, Chem. Lett. 43, 1826-1828 (2014).
Substrate Dependent Ligand Acceleration in Enantioselective Hydrogenation of (E)-2,3-Diarylpropenoic acid on Cinchonidine-Modified Pd/C, T. Mameda, K. Nakai, T. Misaki, Y. Okamoto and T. Sugimura, Catal. Today 245, 129-133 (2014).
Another Role of Copper in the Simmons–Smith Reaction: Copper-Catalyzed Nucleophilic Michael-type Cyclopropanation of α,β-Unsaturated Ketones, Fujii, K., T. Misaki, T. Sugimura, Chem. Lett. 634-636 (2014).

2013

Hydrogenation of 5-alkylidene-2,4-thiazolidiones on Pd/C catalysts under mild conditions: An alternative synthesis route to pioglitazone, Sugimura, T., K. Oie, T. Misaki, Y. Okamoto, K. Tanaka, H. Mori, Catal. Lett. 143, 495-500 (2013).
Enantioselective Oxidation of Alkenylbenzoates Catalyzed by Chiral Hypervalent Iodine(III) To Yield 4-Hydroxyisochroman-1-ones, Shimogaki, M., M. Fujita, T. Sugimura, Eur. J. Org. Chem. 7128-7138 (2013).
Anomalous Ligand Acceleration on Cinchona-Modified Pd/C During Asymmetric Hydrogenation of Properly Substituted Phenylcinnamic Acid, Ogawa, H., T. Mameda, T. Misaki, Y. Okamoto, T. Sugimura, Chem. Lett. 42, 813-815 (2013).
Mitsunobu Reaction with 4-(Diphenylphosphino)benzoic Acid: A Separation-Friendly Bifunctional Reagent that serves as both a Reductant and Pronucleophile, Muramoto, N., K. Yoshino, T. Misaki, T. Sugimura, Synthesis 45, 931-935 (2013).
Arabitol Provided by Lichenous Fungi Enhances Ability to Dissipate Excess Light Energy in a Symbiotic Green Alga under Desiccation, Kosugi, M., H. Miyake, H. Yamakawa, Y. Shibata, A. Miyazawa, T. Sugimura, K. Satoh, S. ItohY. Kashino, Plant Cell Physiol. 54, 1316-1325 (2013).
1,4-Addition Reaction of 5H-Oxazol-4-ones to Allenic Esters and Ketones Catalyzed by Chiral Guanidines, Jin, N., T. Misaki, T. Sugimura, Chem. Lett. 42, 894-896 (2013).
Stereochemical Study on Oxygen-Directed Olefin Oxidation and Subsequent Oxygen Cycization; Difference between Peracid and Metal Oxide-Catalyzed Hydroperoxide in Oxidation, Inoue, A., T. Misaki, M. Fujita, T. Okuyama, T. Sugimura, Tetrahedron: Asymmetry 24, 833-837 (2013).
Total synthesis of (12R)- and (12S)-12-hydroxymonocerins: stereoselective oxylactonization using a chiral hypervalent iodine(III) spe.5cies, Fujita, M., K. Mori, M. Shimogaki, T. Sugimura, RSC Advances, 3, 17717-17725 (2013).

2012

Chiral Guanidine-Catalyzed 1,4-Addition Reaction of 5H-Oxazol-4-ones to Alkynones, T. Misaki, N. Jin, K. Kawano, T. Sugimura, Chem. Lett. 41, 1675 (2012).
Efficient Simmons-Smith cyclopropanation with Zn/Cu and CH2I2, K. Fujii, K. Shiine, T. Misaki, T. Sugimura, Appl. Organomet. Chem. 27, 69 (2012).
Preparation of Pd/C Designed for Chiral Modified Catalyst. Comparison with Pd/TiO2 in Enantioselective Hydrogenation of α-Phenylcinnamic Acid, T. Kubota, H. Ogawa, Y. Okamoto, T. Misaki and T. Sugimura, Applied Catalysis A: General 116, 1168-1175 (2012).
Remote stereocontrol of intramolecular rhodium carbene addition driven by a small and flexible chiral 2,4-pentanediol tether, . Y. Im and T. Sugimura, Tetrahedron 68, 3744-3749 (2012).
Temperature-Independent Stereoselectivity in Intramolecular Cycloaddition of Ketene Generated from Diazoester in Solution and in Vapor Phase. How Entropy Term Governs the Selectivity? Sugimura, T. E. Mitani, T. Tei, T. Okuyama, K. Kamiya, T. Matsui and Y. Shigeta, Bull. Chem. Soc. Jpn. 85, 504-510, (2012).
Theoretical Insight into Stereoselective Reaction Mechanisms of 2,4-Pentanediol-Tethered Ketene-Olefin [2+2] Cycloaddition., Kamiya, K., Matsui, T., Sugimura, T. & Shigeta, Y. J. Phys. Chem. 116, 1168-1175 (2012).
Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III). Fujita, M., Mori, K., Shimogaki, M. & Sugimura, T. Org. Lett. 14, 1294-1297 (2012).

2011

5′-Monohydroxyphylloquinone is the Dominant Naphthoquinone of Photosystem I in the Green Alga Chlamydomonas reinhardtii. Ozawa, S.-i., Kosugi, M., Kashino, Y., Sugimura, T. & Takahashi, Y. Plant Cell Physiol. 53, 237-243 (2011).
Enantioselective Prévost and Woodward reactions using chiral hypervalent iodine(III): swichover of stereochemical cource of an optically active 1,3-dioxan-2-yl cation. Fujita, M., Wakita, M. & Sugimura, T. Chem. Commun. 47, 3983-3985 (2011).
Highly Z-Selective Asymmetric 1,4-Addition Reaction of 5H-Oxazol-4-ones with Alkynyl Carbonyl Compounds Catalyzed by Chiral Guanidines. Misaki, T., Kawano, K. & Sugimura J. Am. Chem. Soc.133, 5695–5697 (2011).

2010

Acceleration of Enantioselective Hydrogenation of Olefins over Pd/C by Cinchonidine as a Chiral Modifier. Comparison with Cinchonine, Pseudo Enantiomer. Sugimura, T. & Ogawa, H. Chem. Lett. 39, 232-233 (2010).
Direct Asymmetric Aldol Reaction of 5H-Oxazol-4-ones with Aldehydes Catalyzed by Chiral Guanidines. Misaki, T., Takimoto, G. & Sugimura, T. J. Am. Chem. Soc. 132, 6286-6287 (2010).
Substrate Adsorption on the Cinchonidine-Modified Pd/C during the Enantio-differentiating Hydrogenation as a Vital Stereocontrol Factor. Misaki, T. et al. J. Mol. Catal. A: Chem, 313, 48-52 (2010).
Enantiodifferentiating endo-Selective Oxylactonization of ortho-Alk-1-enylbenzoate with a Lactate-Derived Aryl-l3-Iodane, M. Fujita,* Y. Yoshida, K. Miyata, A. Wakisaka, T. Sugimura, Angew. Chem. Int. Ed. 49, 7068–7071 (2010).
Enantioselective Hydrogenation of Olefins using Commercially Available Pd/C. Chiral Heterogeneous Catalyst Applicable for High-Throughput Screening. Kim, T. Y. et al. Topics. Catal. 53, 116-122 (2010).
Is Amine Addition Vital for Highly Enantioselective Hydrogenation of a,b-Unsaturated Carboxylic Acid over Cinchonidine-Modified Palladium? Kim, T. Y. & Sugimura, T. J. Mol. Catal. A: Chem. 327, 58-62 (2010).
Ring Closing Metathesis Using Chiral Template Consisting of Hard and Soft Parts. Hakim, S. S. M. A. & Sugimura, T. Macromol. Symp. 293, 10-14 (2010).
Stereocontrol in Radical Cyclization: Change across the Curtin-Hammett Borderline. Hakim, S. S. M. A. & Sugimura, T. Org. Lett. 12, 3626-3629 (2010).