Kamata, Y.; Sugawara, T.; Kikkawa, H.; Hori, R.; Miyashita, Y.; Kanomata, N.; Ono, R.; Kakinuma, M.; Ono, Y.; Sato, Y.; Kashima, T.; Kanetaka, Y.; Maruyama, S.; Takizawa, H. Short Synthesis of [10]Paracyclophanes from Strained [10]Paracyclopha-4,6-diynes Obtained via a Double Negishi Coupling Followed by an Intramolecular Glaser Cyclization. J. Org. Chem.2025, 90, 14949–14956. https://doi.org/10.1021/acs.joc.5c01567
Hirasawa, S.; Kurashima, T.; Hasegawa, T.; Souma, K.; Kanomata, N. Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation. Chem. Lett.2022, 51, 985–988. https://doi.org/10.1246/cl.220299
Hirasawa, S.; Masuda, T.; Mukai, K.; Miyoshi, Y.; Kanomata, N. Asymmetric synthesis of (–)-dehydro-exo-brevicomin with photoisomerisation–intramolecular acetalisation sequence. Org. Biomol. Chem.2021, 19, 6897–6903. https://doi.org/10.1039/D1OB00952D
Ogawa, N.; Furukawa, S.; Kosugi, Y.; Takazawa, T.; Kanomata, N. Biomimetic systems involving sequential redox reactions in glycolysis - the sulfur effect. Chem. Commun.2020, 56, 12917–12920. https://doi.org/10.1039/D0CC05185C
Hirasawa, S.; Mukai, K.; Sakai, S.; Wakamori, S.; Hasegawa, T.; Souma, K.; Kanomata, N.; Ogawa, N.; Aizawa, M.; Emoto, M. Elucidation of racemization process of azaspirene skeleton in neutral aqueous media. J. Org. Chem.2018, 83, 14457–14464. https://doi.org/10.1021/acs.joc.8b02223
Mugishima, N.; Kanomata, N.; Akutsu, N.; Kubota, H. Remote steric effects of C2-symmetric planar-chiral terpyridine ligands on copper-catalyzed asymmetric cyclopropanation reactions. Tetrahedron Lett.2015, 56, 1898–1903. https://doi.org/10.1016/j.tetlet.2015.02.103
Maeda, R.; Wada, T.; Mori, T.; Kono, S.; Kanomata, N.; Inoue, Y. Planar-to-Planar Chirality Transfer in the Excited State. Enantiodifferentiating Photoisomerization of Cyclooctenes Sensitized by Planar-Chiral Paracyclophane. J. Am. Chem. Soc.2011, 133, 10379–10381. https://doi.org/10.1021/ja203781f
Kanomata, N.; Sakaguchi, R.; Sekine, K.; Yamashita, S.; Tanaka, H. Enantioselective Cyclopropanation Reactions with Planar-Chiral Pyridinium Ylides. A Substituent Effect and A Remote Steric Effect. Adv. Synth. Catal.2010, 352, 2966–2978. https://doi.org/10.1002/adsc.201000079
Kanomata, N.; Mishima, G.; Onozato, J. Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation. Tetrahedron Lett.2009, 50, 409–412. https://doi.org/10.1016/j.tetlet.2008.11.021
Kanomata, N.; Suzuki, J.; Kubota, H.; Nishimura, K.; Enomoto, T. Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. Tetrahedron Lett.2009, 50, 2740–2743. https://doi.org/10.1016/j.tetlet.2009.03.095
Kanomata, N.; Yamada, S.; Ohhama, T.; Fusano, A.; Ochiai, Y.; Oikawa, J.; Yamaguchi, M.; Sudo, F. Synthesis of Bridged Nicotinates Having [n](2,5)Pyridinophane Skeletons (n = 8-14). Tetrahedron2006, 62, 4128–4138. https://doi.org/10.1016/j.tet.2006.02.002
Ueda, T.; Kanomata, N.; Machida, H. Synthesis of Planar-Chiral Paracyclophanes via Samarium(II)-Catalyzed Intramolecular Pinacol Coupling. Org. Lett.2005, 7, 2365–2368. https://doi.org/10.1021/ol0506258
Kanomata, N.; Ochiai, Y. Stereocontrol of Molecular Jump-rope: Crystallization-induced Asymmetric Transformation of Planar-chiral Cyclophanes. Tetrahedron Lett.2001, 42, 1045–1048. https://doi.org/10.1016/S0040-4039(00)02043-8
Kanomata, N.; Nakata, T. A Compact Chemical Miniature of a Holoenzyme, Coenzyme NADH Linked Dehydrogenase. Design and Synthesis of Bridged NADH Models and Their Highly Enantioselective Reduction. J. Am. Chem. Soc.2000, 122, 4563–4568. https://doi.org/10.1021/ja992990y
Kamata, Y.; Sugawara, T.; Kikkawa, H.; Hori, R.; Miyashita, Y.; Kanomata, N.; Ono, R.; Kakinuma, M.; Ono, Y.; Sato, Y.; Kashima, T.; Kanetaka, Y.; Maruyama, S.; Takizawa, H. Short Synthesis of [10]Paracyclophanes from Strained [10]Paracyclopha-4,6-diynes Obtained via a Double Negishi Coupling Followed by an Intramolecular Glaser Cyclization. J. Org. Chem.2025, 90, 14949–14956. https://doi.org/10.1021/acs.joc.5c01567
Hirasawa, S.; Kurashima, T.; Hasegawa, T.; Souma, K.; Kanomata, N. Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation. Chem. Lett.2022, 51, 985–988. https://doi.org/10.1246/cl.220299
Hirasawa, S.; Masuda, T.; Mukai, K.; Miyoshi, Y.; Kanomata, N. Asymmetric synthesis of (–)-dehydro-exo-brevicomin with photoisomerisation–intramolecular acetalisation sequence. Org. Biomol. Chem.2021, 19, 6897–6903. https://doi.org/10.1039/D1OB00952D
Ogawa, N.; Furukawa, S.; Kosugi, Y.; Takazawa, T.; Kanomata, N. Biomimetic systems involving sequential redox reactions in glycolysis - the sulfur effect. Chem. Commun.2020, 56, 12917–12920. https://doi.org/10.1039/D0CC05185C
Hirasawa, S.; Mukai, K.; Sakai, S.; Wakamori, S.; Hasegawa, T.; Souma, K.; Kanomata, N.; Ogawa, N.; Aizawa, M.; Emoto, M. Elucidation of racemization process of azaspirene skeleton in neutral aqueous media. J. Org. Chem.2018, 83, 14457–14464. https://doi.org/10.1021/acs.joc.8b02223
Emoto, M.; Yano, K.; Choijamts, B.; Sakai, S.; Hirasawa, S.; Wakamori, S.; Aizawa, M.; Nabeshima, K.; Tachibana, K.; Kanomata, N. Azaspirene analogs inhibit the growth of human uterine carcinosarcoma in vitro and in vivo. Anticancer Res.2015, 35, 2739–2746. https://ar.iiarjournals.org/content/35/5/2739.short
Mugishima, N.; Kanomata, N.; Akutsu, N.; Kubota, H. Remote steric effects of C2-symmetric planar-chiral terpyridine ligands on copper-catalyzed asymmetric cyclopropanation reactions. Tetrahedron Lett.2015, 56, 1898–1903. https://doi.org/10.1016/j.tetlet.2015.02.103
Matsuo, T.; Hattori, T.; Asaba, A.; Inoue, N.; Kanomata, N.; Kikusui, T.; Kobayakawa, R.; Kobayakawa, K. Genetic dissection of pheromone processing reveals main olfactory system-mediated social behaviors in mice. Proc. Natl. Acad. Sci. U. S. A.2015, 112, E311–E320. https://doi.org/10.1073/pnas.1416723112
Maeda, R.; Wada, T.; Mori, T.; Kono, S.; Kanomata, N.; Inoue, Y. Planar-to-Planar Chirality Transfer in the Excited State. Enantiodifferentiating Photoisomerization of Cyclooctenes Sensitized by Planar-Chiral Paracyclophane. J. Am. Chem. Soc.2011, 133, 10379–10381. https://doi.org/10.1021/ja203781f
Izuchi, Y.; Koshino, H.; Hongo, Y.; Kanomata, N.; Takahashi, S. Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring. Org. Lett.2011, 13, 3360–3363. https://doi.org/10.1021/ol2011117
Izuchi, Y.; Kanomata, N.; Koshino, H.; Hongo, Y.; Nakata, T.; Takahashi, S. Formal total synthesis of aspergillide A. Tetrahedron: Asymmetry2011, 22, 246–251. https://doi.org/10.1016/j.tetasy.2011.01.016
Kanomata, N.; Sakaguchi, R.; Sekine, K.; Yamashita, S.; Tanaka, H. Enantioselective Cyclopropanation Reactions with Planar-Chiral Pyridinium Ylides. A Substituent Effect and A Remote Steric Effect. Adv. Synth. Catal.2010, 352, 2966–2978. https://doi.org/10.1002/adsc.201000079
Emoto, M.; Naganuma, Y.; Choijamts, B.; Ohno, T.; Yoshihisa, H.; Kanomata, N.; Kawarabayashi, T.; Aizawa, M. Novel chemoembolization using calcium-phosphate ceramic microsphere incorporating TNP-470, an anti-angiogenic agent. Cancer Sci.2010, 101, 984–990. https://doi.org/10.1111/j.1349-7006.2009.01479.x
Kanomata, N.; Suzuki, J.; Kubota, H.; Nishimura, K.; Enomoto, T. Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. Tetrahedron Lett.2009, 50, 2740–2743. https://doi.org/10.1016/j.tetlet.2009.03.095
Kanomata, N.; Mishima, G.; Onozato, J. Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation. Tetrahedron Lett.2009, 50, 409–412. https://doi.org/10.1016/j.tetlet.2008.11.021
Aizawa, M.; Ohno, T.; Kanomata, N.; Yano, K.; Emoto, M. Anti-Tumorigenesis of Hollow Calcium-Phosphate Microsphere Loaded with Anti-Angiogenic Agent. Key Eng. Mater.2008, 361–363, 1215–1218. https://doi.org/10.4028/www.scientific.net/KEM.361-363.1215
Kanomata, N.; Yamada, S.; Ohhama, T.; Fusano, A.; Ochiai, Y.; Oikawa, J.; Yamaguchi, M.; Sudo, F. Synthesis of Bridged Nicotinates Having [n](2,5)Pyridinophane Skeletons (n = 8-14). Tetrahedron2006, 62, 4128–4138. https://doi.org/10.1016/j.tet.2006.02.002
Ueda, T.; Kanomata, N.; Machida, H. Synthesis of Planar-Chiral Paracyclophanes via Samarium(II)-Catalyzed Intramolecular Pinacol Coupling. Org. Lett.2005, 7, 2365–2368. https://doi.org/10.1021/ol0506258
Kanomata, N.; Oikawa, J. Adsorption-Induced Asymmetric Transformation of Planar-Chiral Pyridinophanes. Tetrahedron Lett.2003, 44, 3625–3628. https://doi.org/10.1016/S0040-4039(03)00699-3
Kanomata, N.; Maruyama, S.; Tomono, K.; Anada, S. A Simple Method Removing 2-Oxazolidinone and 2-Hydroxyethylamine Auxiliaries in Methoxide-Carbonate Systems for Synthesis of Planar-Chiral Nicotinate. Tetrahedron Lett.2003, 44, 3599–3603. https://doi.org/10.1016/S0040-4039(03)00698-1
Kanomata, N.; Ochiai, Y. Stereocontrol of Molecular Jump-rope: Crystallization-induced Asymmetric Transformation of Planar-chiral Cyclophanes. Tetrahedron Lett.2001, 42, 1045–1048. https://doi.org/10.1016/S0040-4039(00)02043-8
Kanomata, N.; Nakata, T. A Compact Chemical Miniature of a Holoenzyme, Coenzyme NADH Linked Dehydrogenase. Design and Synthesis of Bridged NADH Models and Their Highly Enantioselective Reduction. J. Am. Chem. Soc.2000, 122, 4563–4568. https://doi.org/10.1021/ja992990y
Kanomata, N.; Nakata, T. Novel Pyridine-formation Reactions of 2-(Phosphoranylideneamino)acrylaldehydes with Acetylenic Esters. Synthesis of 2-Mono and 2,5-Disubstituted Nicotinates. Heterocycles1998, 48, 2551–2558. https://doi.org/10.3987/COM-98-8314
Kanomata, N. Development of stereocontrol of planar-chirality for N-containing cyclophanes. Fain Kemikaru2003, 44, 5–13 (in Japanese).
Kanomata, N. Studies on Syntheses and Functional Properties of Structurally Unique Nitrogen Aromatics. J. Synth. Org. Chem., Jpn.2003, 61, 352–359 (in Japanese). https://doi.org/10.5059/yukigoseikyokaishi.61.352
Kanomata, N. Coenzyme Mimics for Asymmetric Induction. Design and Syntheses of Bridged NADH Models and Their Highly Enantioselective Reduction. Kagaku To Kogyo1998, 51, 183–186 (in Japanese).
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Dr. Hirasawa — Reception after the Degree Conferment Ceremony (September 16, 2023)
Dr. Hirasawa received his doctoral degree in academic year 2022. This photograph was taken at the reception following the degree conferment ceremony on September 16, 2023.
From left: President Tanaka, Dr. Hirasawa, and Professor Kanomata.
Designing molecular structures to create new functions
At the Functional Organic Chemistry Laboratory (Kanomata Group), Waseda University, we study the relationships between the structures and properties of organic molecules. Our work spans molecular design, synthesis, and functional evaluation. Creating original molecules and understanding how they work are central to our research.
Our main research targets are amines that capture and release carbon dioxide (CO₂), and cyclophanes with distinctive three-dimensional structures. By exploiting molecular reactivity, stereochemistry, dynamics, and interactions with solvents, we seek functions relevant to CO₂ capture and selective organic synthesis. Insights gained through our studies of coenzyme models and the synthesis of bioactive molecules also underpin this molecular design.
2025 | We published a study on the short synthesis and structural analysis of cyclophanes in J. Org. Chem.［2］ 2025 | Our research on CO₂ absorbents based on small oligoamines was featured in the NICHIAS Technical Report.［1］
About the Group and Prospective Students
Our laboratory was established at Meiji University in 1999 and moved to Waseda University in 2005. It is now affiliated with the Department of Chemistry and Biochemistry in the School and Graduate School of Advanced Science and Engineering. Please see the respective pages for our members and location.
Prospective graduate students seeking research supervision in our group should consult the university's official admissions information and contact us for a preliminary discussion before applying.
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Research Overview
We design and synthesize organic molecules with distinctive structures and investigate how those structures give rise to reactivity and function. Alongside organic synthesis, we use spectroscopy, crystal structure analysis, and computational chemistry to study molecular shape, motion, and intermolecular interactions. We apply these insights to the development of CO₂ absorbents, stereochemical control of planar-chiral molecules, and the design of selective chemical reactions.
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Research
We design and synthesize organic molecules with distinctive structures and investigate how those structures give rise to reactivity and function. Alongside organic synthesis, we use spectroscopy, crystal structure analysis, and computational chemistry to study molecular shape, motion, and intermolecular interactions. We apply these insights to the development of CO₂ absorbents, stereochemical control of planar-chiral molecules, and the design of selective chemical reactions.
Molecules and absorbents for both CO₂ capture and release
CO₂ capture requires not only effective uptake, but also the release of captured CO₂ so that the absorbent can be reused. We focus on small oligoamines with multiple amino groups and design capture and release functions through combinations of molecular structure and solvent.［1］
Amine design and neat liquid systems
We study derivatives based on diethylenetriamine (DETA) and triethylenetetramine (TETA), combining secondary and tertiary amine sites. In neat liquid systems without added solvent, we have identified molecules with favorable CO₂ release properties and examined how these properties relate to the structures of CO₂-bound species and intermolecular association.［1］
Ethylene glycol solution systems
In systems containing ethylene glycol (EG), we investigate how amine structure and mixture composition affect CO₂ uptake, absorption rate, and release. EG acts not only as a diluent: in combination with amines, it also participates in the formation of CO₂-capturing species. Comparisons with neat liquid systems highlight the importance of incorporating the solvent into absorbent design.［1］
CO₂ Capture and Release through Reversible Phase Switching
Some mixtures of amines and polar solvents change from two phases to a homogeneous phase upon CO₂ absorption and return to two phases after CO₂ release. We investigate this reversible phase change as a way to create liquid states suited to the capture and release steps.
Schematic of CO₂-responsive phase separation and mixing. This illustrates a mixture showing a reversible phase change; it is not a behavior shared by all absorbents. Enlarge figure
From molecular design to reuse
We combine measurements of CO₂ uptake and release with analysis of CO₂-bound species to understand the origins of absorbent function. By investigating molecular structures, solvents, and additives, we aim to develop absorbents suitable for repeated use.［1］
Synthesis and functions of planar-chiral cyclophanes
Cyclophanes are macrocycles in which a chain bridges distant positions of an aromatic ring. Depending on the arrangement of the bridge and aromatic ring, the molecule may display planar chirality and be non-superimposable on its mirror image. We connect this distinctive stereochemistry and molecular motion to synthetic method development, stereochemical control, and selective reactions.
Short synthesis and analysis of intramolecular structure
In 2025, we reported a three-step synthesis of [10]paracyclophanes and their nitrogen-containing analogues by combining double Negishi coupling, intramolecular Glaser cyclization, and hydrogenation. X-ray crystal structure analysis and quantum chemical calculations on the intermediate cyclophadiynes revealed how nitrogen atoms in the aromatic ring influence the internal geometry. Our results show that electronic effects, as well as steric factors, are important in understanding the distance between the aromatic ring and diyne unit.［2］
This work continues our studies on the synthesis of bridged molecules, including cyclophane synthesis by samarium(II)-mediated intramolecular pinacol coupling and pyridinophane synthesis using our pyridine-ring formation reaction.［12, 13］
Cyclophane synthesis by samarium(II)-mediated intramolecular pinacol coupling. SourceEnlarge figureSynthesis of bridged nicotinic acid derivatives by pyridine-ring formation. SourceEnlarge figure
Molecular motion and control of planar chirality
Some bridged molecules undergo inversion of planar chirality through a motion often described as molecular “rope-skipping.” By combining this isomerization with crystallization, we have developed methods for selectively obtaining a particular stereoisomer. We have also achieved simultaneous stereochemical control of two planar-chiral units through crystallization. Understanding molecular structure and dynamics guides our design of molecular functions.［10, 14］
Crystallization-based stereochemical control of planar-chiral cyclophanes. SourceEnlarge figureSimultaneous stereochemical control of two planar-chiral units. SourceEnlarge figure
Selective reactions using planar chirality
In asymmetric cyclopropanation with planar-chiral pyridinium ylides, we have investigated how bridging structures and substituents influence stereoselectivity. We have also synthesized bridged bipyridine and terpyridine ligands for asymmetric reactions using metal complexes. In cyclopropanation catalyzed by copper complexes of planar-chiral terpyridines, we reported that remote steric factors influence selectivity.［7, 9, 11］
Asymmetric cyclopropanation using planar-chiral pyridinium ylides. SourceEnlarge figureSynthesis of bridged terpyridine ligands. SourceEnlarge figureSynthesis of bridged bipyridine ligands. SourceEnlarge figureMolecular model of a bridged bipyridine with two planar-chiral units · Open videoAsymmetric cyclopropanation using a planar-chiral terpyridine copper complex. SourceEnlarge figure
In collaborative work, we have also examined planar-to-planar chirality transfer in the photoisomerization of cyclooctenes using planar-chiral cyclophanes as photosensitizers.［8］
Photoisomerization and chirality transfer using planar-chiral cyclophanes. SourceEnlarge figure
Redox reactions inspired by coenzyme models
In biological systems, enzymes and coenzymes cooperate to control reaction sites and stereochemistry precisely. We have studied how the functions of the redox coenzyme NAD⁺/NADH can be reproduced using structurally well-defined organic molecules.
Selective hydrogen transfer by bridged NADH models
In NADH models incorporating a pyridinophane framework, the bridge restricts the direction of substrate approach, enabling high stereoselectivity inspired by enzymatic reactions. This work demonstrates the use of bridging structures and planar chirality to control reactive faces and hydrogen transfer.［15, 17］
We have investigated aldehyde oxidation by NAD⁺ models and the resulting formation of NADH models, reproducing glycolytic redox reactions with artificial molecules. Our 2020 study focused on differences in reactivity between sulfur-containing model substrates and their oxygen analogues, providing insights into the role of cysteine residues in biological systems.［5, 16］
Synthesis and stereochemistry of natural products and bioactive molecules
Efficient synthesis of natural products and their analogues with complex stereochemistry provides a foundation for studying molecular function. In addition to reaction selectivity, we have explored synthetic methods that make use of isomerization, crystallization, and photochemical reactions.
Synthesis of azaspirene and stereochemical changes in water
We achieved the total synthesis of racemic azaspirene, an angiogenesis inhibitor, by constructing its spirocyclic framework and using crystallization-induced diastereomer transformation as a key step. We also analyzed the racemization of model molecules in neutral aqueous solution, linking synthesis with solution-phase stereochemistry.［3, 6］
Total synthesis of (±)-azaspirene using crystallization-induced isomerization. SourceEnlarge figureRacemization of the azaspirene framework in water. SourceEnlarge figure
Asymmetric synthesis of a pheromone through photoisomerization
We reported a short asymmetric synthesis of (−)-dehydro-exo-brevicomin (DHB), known as a mouse sex pheromone, using photoisomerization followed by intramolecular acetalization. In this strategy, light generates a geometrical isomer suitable for the subsequent cyclization.［4］
Asymmetric synthesis of (−)-DHB using photoisomerization and intramolecular acetalization. SourceEnlarge figure
References and Public Resources
Kanomata, N. Development and Overview of Small-Oligoamine Absorbents for Highly Efficient CO₂ Capture (translated title). NICHIAS Technical Report2025, No. 4 (Issue 411), 1–6. In Japanese. Full text (PDF, in Japanese)
Kamata, Y.; Sugawara, T.; Kikkawa, H.; Hori, R.; Miyashita, Y.; Kanomata, N.; Ono, R.; Kakinuma, M.; Ono, Y.; Sato, Y.; Kashima, T.; Kanetaka, Y.; Maruyama, S.; Takizawa, H. Short Synthesis of [10]Paracyclophanes from Strained [10]Paracyclopha-4,6-diynes Obtained via a Double Negishi Coupling Followed by an Intramolecular Glaser Cyclization. J. Org. Chem.2025, 90, 14949–14956. https://doi.org/10.1021/acs.joc.5c01567
Hirasawa, S.; Kurashima, T.; Hasegawa, T.; Souma, K.; Kanomata, N. Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation. Chem. Lett.2022, 51, 985–988. https://doi.org/10.1246/cl.220299
Hirasawa, S.; Masuda, T.; Mukai, K.; Miyoshi, Y.; Kanomata, N. Asymmetric synthesis of (–)-dehydro-exo-brevicomin with photoisomerisation–intramolecular acetalisation sequence. Org. Biomol. Chem.2021, 19, 6897–6903. https://doi.org/10.1039/D1OB00952D
Ogawa, N.; Furukawa, S.; Kosugi, Y.; Takazawa, T.; Kanomata, N. Biomimetic systems involving sequential redox reactions in glycolysis - the sulfur effect. Chem. Commun.2020, 56, 12917–12920. https://doi.org/10.1039/D0CC05185C
Hirasawa, S.; Mukai, K.; Sakai, S.; Wakamori, S.; Hasegawa, T.; Souma, K.; Kanomata, N.; Ogawa, N.; Aizawa, M.; Emoto, M. Elucidation of racemization process of azaspirene skeleton in neutral aqueous media. J. Org. Chem.2018, 83, 14457–14464. https://doi.org/10.1021/acs.joc.8b02223
Mugishima, N.; Kanomata, N.; Akutsu, N.; Kubota, H. Remote steric effects of C2-symmetric planar-chiral terpyridine ligands on copper-catalyzed asymmetric cyclopropanation reactions. Tetrahedron Lett.2015, 56, 1898–1903. https://doi.org/10.1016/j.tetlet.2015.02.103
Maeda, R.; Wada, T.; Mori, T.; Kono, S.; Kanomata, N.; Inoue, Y. Planar-to-Planar Chirality Transfer in the Excited State. Enantiodifferentiating Photoisomerization of Cyclooctenes Sensitized by Planar-Chiral Paracyclophane. J. Am. Chem. Soc.2011, 133, 10379–10381. https://doi.org/10.1021/ja203781f
Kanomata, N.; Sakaguchi, R.; Sekine, K.; Yamashita, S.; Tanaka, H. Enantioselective Cyclopropanation Reactions with Planar-Chiral Pyridinium Ylides. A Substituent Effect and A Remote Steric Effect. Adv. Synth. Catal.2010, 352, 2966–2978. https://doi.org/10.1002/adsc.201000079
Kanomata, N.; Mishima, G.; Onozato, J. Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation. Tetrahedron Lett.2009, 50, 409–412. https://doi.org/10.1016/j.tetlet.2008.11.021
Kanomata, N.; Suzuki, J.; Kubota, H.; Nishimura, K.; Enomoto, T. Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. Tetrahedron Lett.2009, 50, 2740–2743. https://doi.org/10.1016/j.tetlet.2009.03.095
Kanomata, N.; Yamada, S.; Ohhama, T.; Fusano, A.; Ochiai, Y.; Oikawa, J.; Yamaguchi, M.; Sudo, F. Synthesis of Bridged Nicotinates Having [n](2,5)Pyridinophane Skeletons (n = 8-14). Tetrahedron2006, 62, 4128–4138. https://doi.org/10.1016/j.tet.2006.02.002
Ueda, T.; Kanomata, N.; Machida, H. Synthesis of Planar-Chiral Paracyclophanes via Samarium(II)-Catalyzed Intramolecular Pinacol Coupling. Org. Lett.2005, 7, 2365–2368. https://doi.org/10.1021/ol0506258
Kanomata, N.; Ochiai, Y. Stereocontrol of Molecular Jump-rope: Crystallization-induced Asymmetric Transformation of Planar-chiral Cyclophanes. Tetrahedron Lett.2001, 42, 1045–1048. https://doi.org/10.1016/S0040-4039(00)02043-8
Kanomata, N.; Nakata, T. A Compact Chemical Miniature of a Holoenzyme, Coenzyme NADH Linked Dehydrogenase. Design and Synthesis of Bridged NADH Models and Their Highly Enantioselective Reduction. J. Am. Chem. Soc.2000, 122, 4563–4568. https://doi.org/10.1021/ja992990y
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Publications
Original Research Articles
Kamata, Y.; Sugawara, T.; Kikkawa, H.; Hori, R.; Miyashita, Y.; Kanomata, N.; Ono, R.; Kakinuma, M.; Ono, Y.; Sato, Y.; Kashima, T.; Kanetaka, Y.; Maruyama, S.; Takizawa, H. Short Synthesis of [10]Paracyclophanes from Strained [10]Paracyclopha-4,6-diynes Obtained via a Double Negishi Coupling Followed by an Intramolecular Glaser Cyclization. J. Org. Chem.2025, 90, 14949–14956. https://doi.org/10.1021/acs.joc.5c01567
Hirasawa, S.; Kurashima, T.; Hasegawa, T.; Souma, K.; Kanomata, N. Total Synthesis of (±)-Azaspirene via Crystallization-induced Diastereomer Transformation. Chem. Lett.2022, 51, 985–988. https://doi.org/10.1246/cl.220299
Hirasawa, S.; Masuda, T.; Mukai, K.; Miyoshi, Y.; Kanomata, N. Asymmetric synthesis of (–)-dehydro-exo-brevicomin with photoisomerisation–intramolecular acetalisation sequence. Org. Biomol. Chem.2021, 19, 6897–6903. https://doi.org/10.1039/D1OB00952D
Ogawa, N.; Furukawa, S.; Kosugi, Y.; Takazawa, T.; Kanomata, N. Biomimetic systems involving sequential redox reactions in glycolysis - the sulfur effect. Chem. Commun.2020, 56, 12917–12920. https://doi.org/10.1039/D0CC05185C
Hirasawa, S.; Mukai, K.; Sakai, S.; Wakamori, S.; Hasegawa, T.; Souma, K.; Kanomata, N.; Ogawa, N.; Aizawa, M.; Emoto, M. Elucidation of racemization process of azaspirene skeleton in neutral aqueous media. J. Org. Chem.2018, 83, 14457–14464. https://doi.org/10.1021/acs.joc.8b02223
Emoto, M.; Yano, K.; Choijamts, B.; Sakai, S.; Hirasawa, S.; Wakamori, S.; Aizawa, M.; Nabeshima, K.; Tachibana, K.; Kanomata, N. Azaspirene analogs inhibit the growth of human uterine carcinosarcoma in vitro and in vivo. Anticancer Res.2015, 35, 2739–2746. https://ar.iiarjournals.org/content/35/5/2739.short
Mugishima, N.; Kanomata, N.; Akutsu, N.; Kubota, H. Remote steric effects of C2-symmetric planar-chiral terpyridine ligands on copper-catalyzed asymmetric cyclopropanation reactions. Tetrahedron Lett.2015, 56, 1898–1903. https://doi.org/10.1016/j.tetlet.2015.02.103
Matsuo, T.; Hattori, T.; Asaba, A.; Inoue, N.; Kanomata, N.; Kikusui, T.; Kobayakawa, R.; Kobayakawa, K. Genetic dissection of pheromone processing reveals main olfactory system-mediated social behaviors in mice. Proc. Natl. Acad. Sci. U. S. A.2015, 112, E311–E320. https://doi.org/10.1073/pnas.1416723112
Maeda, R.; Wada, T.; Mori, T.; Kono, S.; Kanomata, N.; Inoue, Y. Planar-to-Planar Chirality Transfer in the Excited State. Enantiodifferentiating Photoisomerization of Cyclooctenes Sensitized by Planar-Chiral Paracyclophane. J. Am. Chem. Soc.2011, 133, 10379–10381. https://doi.org/10.1021/ja203781f
Izuchi, Y.; Koshino, H.; Hongo, Y.; Kanomata, N.; Takahashi, S. Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring. Org. Lett.2011, 13, 3360–3363. https://doi.org/10.1021/ol2011117
Izuchi, Y.; Kanomata, N.; Koshino, H.; Hongo, Y.; Nakata, T.; Takahashi, S. Formal total synthesis of aspergillide A. Tetrahedron: Asymmetry2011, 22, 246–251. https://doi.org/10.1016/j.tetasy.2011.01.016
Kanomata, N.; Sakaguchi, R.; Sekine, K.; Yamashita, S.; Tanaka, H. Enantioselective Cyclopropanation Reactions with Planar-Chiral Pyridinium Ylides. A Substituent Effect and A Remote Steric Effect. Adv. Synth. Catal.2010, 352, 2966–2978. https://doi.org/10.1002/adsc.201000079
Emoto, M.; Naganuma, Y.; Choijamts, B.; Ohno, T.; Yoshihisa, H.; Kanomata, N.; Kawarabayashi, T.; Aizawa, M. Novel chemoembolization using calcium-phosphate ceramic microsphere incorporating TNP-470, an anti-angiogenic agent. Cancer Sci.2010, 101, 984–990. https://doi.org/10.1111/j.1349-7006.2009.01479.x
Kanomata, N.; Suzuki, J.; Kubota, H.; Nishimura, K.; Enomoto, T. Synthesis of planar-chiral bridged bipyridines and terpyridines by metal-mediated coupling reactions of pyridinophanes. Tetrahedron Lett.2009, 50, 2740–2743. https://doi.org/10.1016/j.tetlet.2009.03.095
Kanomata, N.; Mishima, G.; Onozato, J. Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation. Tetrahedron Lett.2009, 50, 409–412. https://doi.org/10.1016/j.tetlet.2008.11.021
Aizawa, M.; Ohno, T.; Kanomata, N.; Yano, K.; Emoto, M. Anti-Tumorigenesis of Hollow Calcium-Phosphate Microsphere Loaded with Anti-Angiogenic Agent. Key Eng. Mater.2008, 361–363, 1215–1218. https://doi.org/10.4028/www.scientific.net/KEM.361-363.1215
Kanomata, N.; Yamada, S.; Ohhama, T.; Fusano, A.; Ochiai, Y.; Oikawa, J.; Yamaguchi, M.; Sudo, F. Synthesis of Bridged Nicotinates Having [n](2,5)Pyridinophane Skeletons (n = 8-14). Tetrahedron2006, 62, 4128–4138. https://doi.org/10.1016/j.tet.2006.02.002
Ueda, T.; Kanomata, N.; Machida, H. Synthesis of Planar-Chiral Paracyclophanes via Samarium(II)-Catalyzed Intramolecular Pinacol Coupling. Org. Lett.2005, 7, 2365–2368. https://doi.org/10.1021/ol0506258
Kanomata, N.; Oikawa, J. Adsorption-Induced Asymmetric Transformation of Planar-Chiral Pyridinophanes. Tetrahedron Lett.2003, 44, 3625–3628. https://doi.org/10.1016/S0040-4039(03)00699-3
Kanomata, N.; Maruyama, S.; Tomono, K.; Anada, S. A Simple Method Removing 2-Oxazolidinone and 2-Hydroxyethylamine Auxiliaries in Methoxide-Carbonate Systems for Synthesis of Planar-Chiral Nicotinate. Tetrahedron Lett.2003, 44, 3599–3603. https://doi.org/10.1016/S0040-4039(03)00698-1
Kanomata, N.; Ochiai, Y. Stereocontrol of Molecular Jump-rope: Crystallization-induced Asymmetric Transformation of Planar-chiral Cyclophanes. Tetrahedron Lett.2001, 42, 1045–1048. https://doi.org/10.1016/S0040-4039(00)02043-8
Kanomata, N.; Nakata, T. A Compact Chemical Miniature of a Holoenzyme, Coenzyme NADH Linked Dehydrogenase. Design and Synthesis of Bridged NADH Models and Their Highly Enantioselective Reduction. J. Am. Chem. Soc.2000, 122, 4563–4568. https://doi.org/10.1021/ja992990y
Kanomata, N.; Nakata, T. Novel Pyridine-formation Reactions of 2-(Phosphoranylideneamino)acrylaldehydes with Acetylenic Esters. Synthesis of 2-Mono and 2,5-Disubstituted Nicotinates. Heterocycles1998, 48, 2551–2558. https://doi.org/10.3987/COM-98-8314
Kanomata, N. Development and Overview of Small-Oligoamine Absorbents for Highly Efficient CO₂ Capture (translated title). NICHIAS Technical Report2025, No. 4 (Issue 411), 1–6. In Japanese. Full text (PDF, in Japanese)
Kanomata, N. Development of stereocontrol of planar-chirality for N-containing cyclophanes. Fain Kemikaru2003, 44, 5–13 (in Japanese).
Kanomata, N. Studies on Syntheses and Functional Properties of Structurally Unique Nitrogen Aromatics. J. Synth. Org. Chem., Jpn.2003, 61, 352–359 (in Japanese). https://doi.org/10.5059/yukigoseikyokaishi.61.352
Kanomata, N. Coenzyme Mimics for Asymmetric Induction. Design and Syntheses of Bridged NADH Models and Their Highly Enantioselective Reduction. Kagaku To Kogyo1998, 51, 183–186 (in Japanese).
Selected Patents
Kanomata, N.; Jung, H. Carbon Dioxide Absorbent (translated title). Japanese Patent Application No. 2025-037728, filed March 10, 2025.
Kanomata, N.; Akutsu, Y. Carbon Dioxide Absorbent (translated title). Japanese Patent Application No. 2025-037727, filed March 10, 2025.
Sato, H.; Kanomata, N.; Yubuchi, T. Substituted Piperazine Compounds, and Absorbents and Absorbent Solutions for Acid Gases (translated title). JP2018140981A, September 13, 2018 (application publication); JP6860147B2, April 14, 2021 (granted patent publication). Patent record
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Members, Fall Semester 2026
Group photograph, Spring Semester 2026
Professor
Faculty of Science and Engineering (Department of Chemistry and Biochemistry, School of Advanced Science and Engineering)
Doctoral Program, Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering
Yuki Kamata
Graduate Students (Master's Program)
Master's Program, Department of Chemistry and Biochemistry, Graduate School of Advanced Science and Engineering
Yui Akutsu
Hayato Itagane
Takumi KashimaLab Leader
Yamato Kanetaka
Hyunyoung Jung
Maho KumaiLab Manager
Itta Sasaki
Taichi Seki
Diego Asencio
Undergraduate Students
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering
Daigo Noguchi
Sayuki Sakai
Mirai SekiStudent Leader, 2026–2027
Kota Horiguchi
Yu Masuda
Adjunct Researchers
Narihito OgawaDepartment of Applied Chemistry, School of Science and Technology, Meiji University / Research Institute for Science and Engineering, Waseda University
Shinnosuke WakamoriDepartment of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture / Research Institute for Science and Engineering, Waseda University
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Faculty
Nobuhiro Kanomata
Nobuhiro Kanomata
Professor, Faculty of Science and Engineering, Waseda University Department of Chemistry and Biochemistry, School of Advanced Science and Engineering Doctor of Engineering, Waseda University
Education and Career
1981-85
Department of Chemistry, School of Science and Engineering, Waseda University
1985-87
Master's Program, Graduate School of Science and Engineering, Waseda University
1987-90
Doctoral Program, Graduate School of Science and Engineering, Waseda University
1990
Doctor of Engineering, Waseda University
1990-92
Research Associate, Department of Chemistry, School of Science and Engineering, Waseda University
1992-94
Postdoctoral Researcher, Department of Chemistry, The University of Chicago
1994-97
Special Postdoctoral Researcher, RIKEN
1997-98
Research Collaborator, RIKEN
1998-2001
Researcher, PRESTO, Japan Science and Technology Corporation
1999-2005
Associate Professor, Department of Industrial Chemistry, School of Science and Technology, Meiji University
2005-2007
Professor, Department of Chemistry, Faculty of Science and Engineering, Waseda University
2007–present
Professor, Faculty of Science and Engineering, Waseda University (reorganized as the Department of Chemistry and Biochemistry, School of Advanced Science and Engineering)
2020-2024
Dean, School and Graduate School of Advanced Science and Engineering, Waseda University
Concurrent Appointments and Collaborative Research
1998-99
Visiting Researcher, RIKEN
1999-2004
Guest Researcher, RIKEN
2003-2005
Collaborative Researcher, National Institute of Informatics
2004-2006
Collaborative Researcher, RIKEN
Awards
1997 — Research Planning Award (Banyu Pharmaceutical), Society of Synthetic Organic Chemistry, Japan
2002 — Award for Encouragement of Research in Synthetic Organic Chemistry, Society of Synthetic Organic Chemistry, Japan
Research Areas and Keywords
Research Areas: Functional Organic Chemistry, Structural Organic Chemistry, and Heterocyclic Chemistry
Keywords: Planar-Chiral Cyclophanes, Pyridinophanes, Control of Planar Chirality, Biomimetic Reactions, Organocatalysis, and CO₂ Capture and Release Using Low-Molecular-Weight Amines
Writing Scientific Papers: Paragraphs and Abstracts
Graduate Courses
Research in Functional Organic Chemistry; Advanced Functional Organic Chemistry; Seminars in Functional Organic Chemistry A–D; Special Laboratory in Chemistry and Biochemistry
The Chemical Society of Japan; The Society of Synthetic Organic Chemistry, Japan; American Chemical Society; The Pharmaceutical Society of Japan; Catalysis Society of Japan; International Society of Heterocyclic Chemistry
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Alumni
Alumni of the Functional Organic Chemistry Laboratory at Meiji University and Waseda University are listed by academic year of graduation or degree completion, with their university and degree category.
Alumni and photographs are grouped by academic year (April–March). For example, March 2026 graduates belong to academic year 2025. “Student Leader” preserves the underlining used in the original roster. Roman-alphabet spellings have been checked against available laboratory records and related sources.
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Alumni Destinations
Further study and employment destinations of our alumni are grouped by university and degree category.
This record preserves the existing destination lists. The Waseda University list is dated September 21, 2023; the Meiji University list has no stated update date. University, graduate school, and employer names reflect those in the original record. Numbers in parentheses indicate the number of alumni listed for each further-study destination.
Waseda University Alumni
Coverage stated on the original page: graduates from 2006 onward
Bachelor's Graduates
Further Study
Graduate School of Science and Engineering, Waseda University (3)
Graduate School of Advanced Science and Engineering, Waseda University (48)
Graduate School of Science, Osaka University (1)
Interdisciplinary Graduate School of Engineering Sciences, Kyushu University (1)
Graduate School of Science, Kyoto University (1)
Graduate School of Engineering, The University of Tokyo (1)
Graduate School of Science, The University of Tokyo (7)
Graduate School of Agricultural and Life Sciences, The University of Tokyo (3)
Graduate School of Pharmaceutical Sciences, The University of Tokyo (2)
Graduate School of Science, Tokyo Institute of Technology (1)
Graduate School of Life Sciences, Tohoku University (1)
Employment
NTT Communications Corporation
The Shizuoka Bank
Panasonic Electric Works Co., Ltd.
Mynavi Corporation
Mizuho Research & Technologies, Ltd.
Musashi Engineering, Inc.
The Monogatari Corporation
Master's Graduates
Further Study
Graduate School of Advanced Science and Engineering, Waseda University (3)
Employment
ADEKA Corporation
IHI Inspection & Instrumentation Co., Ltd.
Asahi Kasei Corporation
Asahi Glass Co., Ltd.
Ajinomoto Fine-Techno Co., Inc.
Astellas Pharma Inc.
ENEOS Corporation
Godo Shigen Sangyo Co., Ltd.
Shiseido
Sharp Corporation
Shin-Etsu Chemical Co., Ltd.
Sumitomo Chemical Co., Ltd.
Sumitomo Corporation
Sekisui Chemical Co., Ltd.
SoftBank Corp.
Daiichi Kigenso Kagaku Kogyo Co., Ltd.
TonenGeneral Sekiyu K.K.
Toyo Quality One Corporation
Toray Industries, Inc.
Dow Corning Toray Co., Ltd.
Nichia Corporation
Barclays Securities Japan Limited
Hitachi Chemical Co., Ltd.
Fujikura Kasei Co., Ltd.
Bushu Pharmaceuticals Ltd.
Bridgestone Corporation
FUJIFILM Corporation
Mitsubishi Gas Chemical Company, Inc.
Mitsubishi Chemical Corporation
Mitsubishi Materials Corporation
Tokiwa High School, Gunma Tokiwa Gakuen
Meiji University Alumni
Coverage stated on the original page: graduates from 2000 through 2006
Bachelor's Graduates
Further Study
Graduate School of Science and Technology, Meiji University (31)
Graduate School of Science and Engineering, Tokyo Institute of Technology (2)
Graduate School of Engineering, Tokyo University of Agriculture and Technology (1)
Graduate School of Engineering, Yokohama National University (1)
Graduate School of Materials Science, Nara Institute of Science and Technology (2)
Interdisciplinary Graduate School of Engineering Sciences, Kyushu University (1)
Graduate School of Science and Engineering, University of Toyama (1)
Graduate School of Engineering, Nagoya University (1)
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Photographs by Academic Year
Explore records of our laboratory from academic year 1999 to the present. Select a year for group photographs and photographs of graduation and degree conferment ceremonies.
Department of Chemistry, School of Science and Engineering, Waseda University
Academic Year 2005 — Degree Conferment and Farewell Party
A record of academic year 2005 (April 2005–March 2006).
Academic year 2005 — Degree Conferment and Farewell Party 1 · Enlarge photographAcademic year 2005 — Degree Conferment and Farewell Party 2 · Enlarge photographAcademic year 2005 — Degree Conferment and Farewell Party 3 · Enlarge photograph
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Academic Year 2007 — Degree Conferment and Farewell Party
A record of academic year 2007 (April 2007–March 2008).
Academic year 2007 — Degree Conferment and Farewell Party 1 · Enlarge photographAcademic year 2007 — Degree Conferment and Farewell Party 2 · Enlarge photographAcademic year 2007 — Degree Conferment and Farewell Party 3 · Enlarge photographAcademic year 2007 — Degree Conferment and Farewell Party 4 · Enlarge photograph
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University
Links and Research Resources
University services and resources for literature searches, experiments and teaching. External links open in a new tab.
Some databases and full-text articles require institutional access or an individual account. Japanese-language destinations are marked where applicable.
Research reagents, chemical compounds and antibodies; structure search is also linked. English link: US regional site; use the Japanese site for domestic purchasing.
