Language：English   Publishing type：Research paper (scientific journal)  

C–H functionalization has recently received considerable attention because C–H functionalization during the late-stage transformation is a strong and useful tool for the modification of the bioactive compounds and the creation of new active molecules. Although a carbene transfer reaction can directly convert a C–H bond to the desired C–C bond in a stereoselective manner, its application in late-stage material transformation is limited. Here, we observed that the iridium–salen complex 6 exhibited efficient catalysis in asymmetric carbene C–H insertion reactions. Under optimized conditions, benzylic, allylic, and propargylic C–H bonds were converted to desired C–C bonds in an excellent stereoselective manner. Excellent regioselectivity was demonstrated in the reaction using not only simple substrate but also natural products, bearing multiple reaction sites. Moreover, based on the mechanistic studies, the iridium-catalyzed unique C–H insertion reaction involved rate-determining asynchronous concerted processes.

DOI： 10.1021/acs.joc.2c00470

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Repository Public URL： http://hdl.handle.net/2324/4794501

Language：English   Publishing type：Research paper (scientific journal)  

A water molecule is one of the ideal oxygen sources in organic synthesis. If a theoretical stoichiometric amount of water can be activated to the reactive intermediates such as metal(oxo) species and inserted to C–H bond, the C¬–H oxidation would be an efficient and useful tool for the oxygen functionalization, especially isotopically oxygen-labeled functional groups. Herein, we found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of iodobenzene(dicarboxylate) and can be used to the oxygen source for non-heme-type ruthenium(bpga)-catalyzed site-selective C–H oxygenation. Under that Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C–H bonds in various compounds, even complicated natural products, can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as D-[3-17O/18O]-mannose can be prepared in a multi-gram scale.

DOI： 10.1021/acs.orglett.1c02812

Repository Public URL： http://hdl.handle.net/2324/4794494

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.orglett.0c01373

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/ajoc.201900602

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.orglett.0c00048

Language：English   Publishing type：Research paper (scientific journal)  

Herein, we developed a Ru(II)(BPGA) complex that could be used to catalyze chemo- and site-selective C−H oxidation. The described ruthenium complex was designed by replacing one pyridyl group on tris(2-pyridylmethyl)amine with an electron-donating amide ligand that was critical for promoting this type of reaction. More importantly, higher reactivities and better chemo-, and site-selectivities were observed for reactions using the cis-ruthenium complex rather than the trans-one. This reaction could be used to convert sterically less hindered methyne and/or methylene C−H bonds of a various organic substrates, including natural products, into valuable alcohol or ketone products.

DOI： 10.1002/asia.202000134

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.160680

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.201310426

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.201208906

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ol302095r

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.201201848

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1039/c2cc32997b

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.201101801

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ja104184r

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/ja802561t

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/anie.200604385

Language：English   Publishing type：Research paper (scientific journal)  

(R,R)-Ru(salen)(CO) complex (1) was found to catalyze enantioselective aziridination of conjugated terminal olefins and allylic C-H amination of conjugated olefins bearing geminal- and/or trans-substituent(s) in the presence of p-toluenesulfonyl azide.

Language：English   Publisher：Organic and Biomolecular Chemistry  

Despite the remarkable developments of the Ugi reaction and its variants, the use of ammonia in the Ugi reaction has long been recognized as impractical and unsuccessful. Indeed, the ammonia-Ugi reaction often requires harsh reaction conditions, such as heating and microwave irradiation, and competes with the Passerini reaction, thereby resulting in low yields. This study describes a robust and practical ammonia-Ugi reaction protocol. Using originally prepared ammonium carboxylates in trifluoroethanol, the ammonia-Ugi reaction proceeded at room temperature in high yields and showed a broad substrate scope, thus synthesizing a variety of α,α-disubstituted amino acid derivatives, including unnatural dipeptides. The reaction required no condensing agents and proceeded without racemization of the chiral stereocenter of α-amino acids. Furthermore, using this protocol, we quickly synthesized a novel dipeptide, d-Leu-Aic-NH-CH2Ph(p-F), which exhibited a potent inhibitory activity against α-chymotrypsin with a Ki value of 0.091 μM.

DOI： 10.1039/d4ob00924j

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Publisher：Advanced Synthesis and Catalysis  

The prospect of developing methods to control the reactivity of metal(oxo) holds appeal for both synthetic and bioinorganic chemistry. In this study, we observed that carboxylic acids enhance reactivity in C−H oxidation by forming hydrogen bonds with the oxo ligand, thereby increasing the basicity and electrophilicity of the oxo intermediate. Additionally, we discovered that H-dicarboxylate ligands, such as oxalate, malonate, and maleate, significantly improve the catalyst turnover frequency (up to 760/h) in unactivated C(sp3)−H oxidation. Furthermore, the addition of maleic acid was also found to activate Fe and Mn(pdp)-catalysed C−H oxygenation. Notably, Ru(bpga)(H-maleate)2 3-catalyzed C−H functionalization exhibited a broad functional group tolerance, including bromine, hydroxyl, benzoate, nitro, nitryl, sulfonate, imide, sulfonylamide, and carbamate, yielding up to 98% in a site- and chemoselective manner with only 0.1–2.0 mmol% loading.

DOI： 10.1002/adsc.202301453

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/tcr.202300156

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Publisher：Tetrahedron Letters  

We present here that the use of bioxazoline ligands improved the enantioselectivity of the palladium-catalyzed chain-walking cycloisomerization of 1,n-dienes. The new system was applied to the asymmetric chain-walking cycloisomerization of a variety of 1,n-dienes as well as asymmetric hydrosilylation/cyclization of a 1,8-diene.

DOI： 10.1016/j.tetlet.2022.154292

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media {LLC}  

Plant extracts are rich in a wide variety of molecules with diverse biological activities. Chemical engineering of plant extracts has provided a straightforward and simultaneous synthetic route for artificial molecules derived from plant products. This study achieved the synthesis of 13 natural product-like molecules by the Ugi multicomponent reaction using plant extracts as substrates. In particular, the engineering of a mixture of plant extracts demonstrated a unique synthetic route to a series of natural product hybrids, whereby otherwise unencountered naturally occurring molecules of different origins were chemically hybridized in complex media. Even though these reactions took place in complex media containing plant extracts, the well-designed process achieved a good conversion efficiency (~ 60%), chemoselectivity, and reproducibility. Additionally, some of the Ugi adducts exhibited promising inhibitory activity toward protease.

DOI： 10.1038/s41598-022-19579-6

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Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

DOI： 10.3390/molecules27010225

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Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1021/acs.joc.8b00190

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.2011.1343

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1016/j.tetlet.2009.02.169

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.2008.632

Language：English   Publishing type：Research paper (scientific journal)  

Ru(salalen)(CO)₂ complexes were found to serve as catalysts for asymmetric sulfimidation under irradiation, and high enantioselectivity (up to 90% ee) was obtained. In addition, the structures of two Ru(salalen)(CO) ₂ complexes that carry the ligands of the same configuration but induce opposite asymmetry to each other, were determined by X-ray diffraction analysis.

DOI： 10.1246/cl.2007.1092

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1002/asia.200600363

Language：English   Publishing type：Research paper (scientific journal)  

[N,N'-ethylenebis(salicylideneimine)] ligands are readily prepared by condensation of o-hydroxybenzaldehydes and diamines, and are known to form a variety of metal complexes. In the last decade, optically active metallosalen complexes have emerged as very useful catalysts for various asymmetric transformations, and high enantioselectivities and unique catalytic properties have been acquired by dictating the aldehyde, diamine, and central metal units. Of particular note is their tremendous contribution to recent rapid progress in atom-efficient asymmetric reactions, which emit no waste or only nontoxic byproducts of small molecular weight such as water and nitrogen. Described in this review are (1) asymmetric and chemoselective aerobic oxidations under photoactivation, (2) asymmetric oxidations with hydrogen peroxide regulated by cis-beta salen complexes, (3) enantio- and diastereo-selective cyclopropanations of alkenes with diazo compounds, (4) asymmetric aminations with azides, and (5) asymmetric ring opening reactions of epoxides and addition reactions to carbonyl substrates by dual activation methods.

Language：English   Publishing type：Research paper (scientific journal)  

Baeyer-Villiger oxidation of racemic bicyclic cyclobutanones with Zr[bis(salicylidene)ethylenediaminato] (salen) complex 1 as catalyst in the presence of a urea-hydrogen peroxide adduct was found to proceed enantiospecifically. The enantiotopos selection in the oxidation was governed primarily by the Zr(salen) catalyst, although migratory aptitude (methine > methylene > methyl) in Baeyer-Villiger oxidation affected the selection to a varied extent, depending on the substrate structures; one enantiomer of cyclobutanones gave exclusively a normal lactone expected from the migratory aptitude, and the other enantiomer gave an abnormal lactone preferentially, the formation of which is counter to the migratory aptitude. Furthermore, the rates of abnormal lactone formation were found to be faster than those of normal lactone formation in most of the oxidations examined. For example, the enantiomer of racemic bicyclo[3.2.0]heptan-6-one giving an abnormal lactone reacted 2.2 times faster than the other enantiomer giving a normal lactone. To our knowledge, this example of chemocatalytic Baeyer-Villiger oxidation giving an abnormal lactone in preference to a normal lactone has been previously unreported. This unusual behavior is likely to be attributable to strict control of stereoelectronic demand in Baeyer-Villiger oxidation and chiral recognition by complex 1.

DOI： 10.1073/pnas.0306992101

Language：English   Publishing type：Research paper (scientific journal)  

Pentagonal bipyramidal Hf(salen) complex I was found to serve as a catalyst for 1,4-addition reaction of thiol to N-(2alkenoyl)-2-oxazolidinones.

DOI： 10.1016/j.tetlet.2004.01.095

Language：English   Publishing type：Research paper (scientific journal)  

A new robust fluorinated (OC)Ru(salen) complex was designed on the basis of an X-ray structure of its parent complex to show improved turnover numbers (up to 878) and enantioselectivities (up to 99%) in aziridination reactions using p-toluenesulfonyl (Ts) or p-nitrobenzenesulfonyl (Ns) azide as the nitrene precursor; the latter is synthetically advantageous since the Ns group is N-protecting and can be removed under mild conditions.

DOI： 10.1039/b407693a

Language：English   Publishing type：Research paper (scientific journal)  

Spectroscopic analysis of imidation of alkyl aryl Sulfides with N-2,2,2-trichloro-1,1-diniethylethyloxycarbonyl azide 2 in the presence of (OC)Ru(salen) complex 1 strongly suggests that an addition compound of the azide 2 to 1 is the active species for the imidation, while the addition compound undergoes the undesired intrarnolecular C-H insertion onto the salen ligand of the complex in the absence of sulfide, directly or via the corresponding nitrene-ruthenium Species.

DOI： 10.1016/j.tetlet.2003.08.108

Language：English   Publishing type：Research paper (scientific journal)  

Intramolecular cyclopropanation of alkenyl alpha-diazoacetates and alkenyl diazomethyl ketones was examined by using optically active (ON+)Ru(11)(salen) and Co(II)(salen) complexes as catalysts. For the cyclization of 2-alkenyl alpha-diazoacetates, Co(II)(salen) complexes 9 and 10 were found to be superior catalysts to the corresponding (ON+)Ru(11)(salen) complexes 4 and 5. On the other hand, (ON+)Ru(II)(salen) complex 2 was found to be the catalyst of choice for the cyclization of 3-alkenyl diazomethyl ketones, and complex 4 was found to be a good catalyst for the cyclization of (E)-4-alkenyl diazomethyl ketones. The present study demonstrates that metallosalen complexes, especially optically active (ON+)Ru(II)(salen) and Co(11)(salen) complexes, can serve as efficient catalysts for the cyclization of alkenyl diazocarbonyl compounds, if a suitable salen ligand is used as the chiral auxiliary.

DOI： 10.1016/S0957-4166(03)00167-8

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1246/cl.2003.354

Language：English   Publishing type：Research paper (scientific journal)  

Enantioselective imidation of alkyl aryl sulfides with N-alkoxycarbonyl azide as a nitrene precursor was effected by using (OC)Ru(salen) complex 1 as catalyst. The steric and electronic nature of the N-alkoxycarbonyl group was found to strongly affect the enantioselectivity and the reaction rate, and high enantioselectivity (up to 99% ee) and good chemical yields were achieved by using 2,2,2-trichloro-1,1-dimethylethoxycarbonyl azide as the nitrene precursor at room temperature.

DOI： 10.1016/S0040-4039(03)00609-9

Language：English   Publishing type：Research paper (scientific journal)  

(OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99% ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80% ee.

DOI： 10.1002/chir.10156

Language：English   Publishing type：Research paper (scientific journal)  

Intramolecular cyclopropanation of alkenyl diazoketones was found to proceed in a highly enantioselective manner by using optically active (nitroso)(salen)ruthenium(II) complex 1 as the catalyst under photo-irradiation.

DOI： 10.1246/cl.2002.846

Language：Japanese   Publishing type：Research paper (scientific journal)  

(R,R)-Zr(salen) complex was found to serve as an efficient catalyst for asymmetric Baeyer-Villiger oxidation of pro-chiral and racemic ketones using urea-hydrogen peroxide as the terminal oxidant: for example, high enantioselectivity of 87% ee was achieved in the Baeyer-Villiger reaction of 3-phenylcyclobutanone.

DOI： 10.1016/S0040-4039(02)00831-6

Language：English   Publishing type：Research paper (scientific journal)  

A series of chiral (salen)cobalt(III) complexes (salen = [bis(salicylidene)ethylenediaminato] = [{2,2'-(ethane-1,2-diyl)bis[ (nitrilo-kappaN)methylidyne]bis[phenolato-kappaO]}(2 -)]) of cis-beta structure were prepared and used for the enantioselective Baeyer-Villiger oxidation of prochiral cyclobutanones with hydrogen peroxide as terminal oxidant. Both cationic (salen)cobalt(III) and neutral iodo(salen)cobalt(III) complexes 3-5 and 7-12, respectively, all having a chiral binaphthalenediamine unit, were found to be effective catalysts for the enantioselective Baeyer-Villiger oxidation (Tables 1, 3, and 4). In particular, complex 8 bearing electron-withdrawing F-atoms showed a good level of enantioselectivity (75-79% ee) in the reactions of 3-arylcyclobutanones (Scheme 4). On the other hand, complex 12 bearing Bu-t groups at C(3) and C(3') and electron-withdrawing NO2 groups at C(5) and C(5') (trivial numbering) exhibited a high enantioselectivity of 98% ee in the reaction of a tricyclic cyclobutanone (Table 4).

DOI： 10.1002/1522-2675(200210)85:10<3078::AID-HLCA3078>3.0.CO;2-1

Language：English   Publishing type：Research paper (scientific journal)  

An (OC)Ru(II)(salen) complex was found to catalyze imidation of alkyl aryl sulfides in the presence of azide with high enantioselectivity as well as good chemical yield.

DOI： 10.1016/S0040-4039(01)01448-4

Language：Japanese   Publishing type：Research paper (scientific journal)  

A cationic Co(III)(salen) complex of cis-beta -structure was found to serve as an efficient catalyst for asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanone using hydrogen peroxide as a terminal oxidant. Good enantio selectivity up to 78% ee was achieved.

DOI： 10.1016/S0040-4039(01)01445-9

Language：English   Publishing type：Research paper (scientific journal)  

Optically active Co(II)-salen complexes (5 and 7) were found to catalyze highly enantioselective intramolecular cyclopropanation of 2-alkenyl alpha -diazoacetates in the presence of N-methylimidazole under high substrate concentration.

DOI： 10.1016/S0040-4039(01)00218-0

Language：English   Publishing type：Research paper (scientific journal)  

Language：Japanese   Publishing type：Research paper (scientific journal)  

Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Dials-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (RP)-(salen)chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and -manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes bearing a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-beta -structure.

Language：English   Publishing type：Research paper (scientific journal)  

Language：English   Publishing type：Research paper (scientific journal)  

Intramolecular cyclopropanation of (E)-2-alkenyl alpha -diazoacetates was carried out with good to high enantioselectivity by using (nitroso)(salen)ruthenium(II) complexes as catalysts under photo-irradiation.

Language：English   Publishing type：Research paper (scientific journal)  

Optically active (nitroso)(salen)ruthenium(II) chloride (2) was found to be an efficient catalyst for aerobic oxidation of racemic secondary alcohols under irradiation with a halogen or fluorescent lamp, which proceeded with good enantiomer-differentiation (k(rel) = 11-20). Furthermore, no epoxidation was observed in the oxidation of racemic 4-phenyl-3-buten-2-ol.

DOI： 10.1016/S0040-4039(00)00787-5

Language：English   Publishing type：Research paper (scientific journal)  

Cyclopropanation of styrene with alpha-diazoacetate in the presence of (R,R)-(salen)ruthenium complex 4 in THF which dissolves the complex exhibits remarkable cis- and enantio-selectivity [cis:trans=97:3, >97% ee (1S,2R)], while the same reaction in hexane which does not dissolve it shows good but opposite sense of enantioselectivity [-83% ee (1R,2S)] together with moderate cis-selectivity (cis:trans=68:32). In homogeneous and heterogeneous conditions, (salen)ruthenium complexes are considered to have different ligand-conformation which, in turn, causes the opposite sense of enantioface selectivity in the cyclopropanation.

DOI： 10.1016/S0040-4020(00)00273-8

Language：English   Publishing type：Research paper (scientific journal)  

The reactions of styrene derivatives and t-butyl alpha-diazoacetate using (R,R)-(salen)cobalt(II) complex 6 as a catalyst in the presence of N-methylimidazole gave the corresponding cyclopropanecarboxylates with excellent enantio- (>95% ee) and high cis-stereoselectivity (98%) as well as good chemical yields.

DOI： 10.1016/S0040-4039(00)00433-0

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-1999-2782

Language：English   Publishing type：Research paper (scientific journal)  

DOI： 10.1055/s-1999-2955

Event date： 2022.12

Language：English   Presentation type：Oral presentation (general)  

Venue：Singapore、Innovis Building（2 Fusionoplis Way）   Country：Japan  

Event date： 2022.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：九州大学馬出キャンパス   Country：Japan  

Event date： 2022.9

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

有機化合物の後期修飾は、生物活性物質などの機能性化合物の改質において有効な手法である。しかし、複雑な天然物などの機能性物質の後期修飾は、反応位置制御が難しいなど多くの課題が残されている。一方、今回、演者らは、ルテニウム錯体が、水の酸素原子を酸素源に高位置選択的なC–H酸化反応の優れた触媒となることを見出した。同反応では、複雑な化合物でも水の酸素原子を望みの位置に定量的に導入することが可能である。

Event date： 2021.2

Language：English   Presentation type：Oral presentation (general)  

Country：United States  

Event date： 2018.11

Language：English  

Venue：九州大学医学部　百年講堂（福岡）   Country：Japan  

Event date： 2018.11

Language：English   Presentation type：Oral presentation (general)  

Venue：九州大学医学部　百年講堂（福岡）   Country：Japan  

Carbon–hydrogen bonds are ubiquitous and abundant in organic molecule. If that C–H bond can be directly converted to desired function group with stereo- and site-selective manner, C– H bond functionalization would really strong and efficient tool in organic synthesis. Recently, we found that ruthenium-salen complexes are efficient catalyst for nitrene and oxo transfer reactions using highly atom-economic oxidants such as azide and dioxygen.
(OC)ruthenium(II)-salen complex decompose azide compounds to corresponding nitrene intermediates with co-producing nitrogen gas as the by-product. Obtained ruthenium-nitrene can insert benzylic and allylic C–H bond with excellent site- and stereo-selective manner. Interestingly, ruthenium-catalysed C–H amination undergoes exclusively at methylene C–H bond on ethyl group. 1
On the other hand, (aqua)ruthenium(III) complex can activate dioxygen to superoxide intermediate via single electron transfer (SET). Obtained superoxide delocalized radical cation intermediate.2 This mechanism suggests that, arenols could be oxidized to the electrophilic radical intermediate and then converted to the desired bis(arenol)s. Based on this suggestion, we conducted the oxidative coupling of arenols using dioxygen as a hydrogen accepter. Under ruthenium-catalyzed aerobic conditions, arenols can converted to bis(arenol)s with good to high enantioselectivity. Under that conditions, C3-substituted 2-naphthols using C7-substituted 2-naphthols or phenol derivatives gave the cross-coupling products with good to high chemoselectivity, irrespective with electron nature of each arenols.

Event date： 2018.11

Language：Japanese  

Venue：九州大学西新プラザ（福岡）   Country：Japan  

Event date： 2018.11

Language：Japanese  

Venue：九州大学西新プラザ（福岡）   Country：Japan  

Event date： 2018.9

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2018.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：ホテル竹島（蒲郡）   Country：Japan  

Event date： 2018.8 - 2018.9

Language：English  

Country：Japan  

Event date： 2018.8 - 2018.9

Language：English  

Venue：Keio (Yokohama)   Country：Japan  

Event date： 2018.6

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北九州   Country：Japan  

Event date： 2018.6

Language：English   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2018.5

Language：English   Presentation type：Oral presentation (general)  

Venue：Venue: Lecture Hall, 1st floor, Junmou Building, SIOC, 345 Lingling Lu, Shanghai   Country：Japan  

Event date： 2018.5

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：北海道大学クラーク講堂   Country：Japan  

Event date： 2017.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：神奈川大学 横浜キャンパス3号館   Country：Japan  

アレノール類の不斉酸化的カップリング反応は、光学活性なビス（アレノール）類を得る最も直截的かつ有用な手法である。
しかし、従来の方法では、非対称ビス（アレノール）類を得ることは極めて難しく、アレノール間に大きな酸化電位差を付けなければならなかった。
一方、我々は、キラルなルテニウム触媒はユニークな触媒活性を示すことを今回見出した。
すなわち、ルテニウム触媒を用いると２つのアレノール間に大きな電位差がなくても、それぞれの置換様式の違いを認識して非対称ビス（アレノール）を選択的に与えることを明らかにした。

Event date： 2017.9

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：東北大学川内キャンパス　東北大学百周年記念会館 川内萩ホール   Country：Japan  

Event date： 2017.2

Language：English   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2016.7

Language：English   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2014.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：名古屋（名古屋大学）   Country：Japan  

Event date： 2013.11

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2012.10

Language：Japanese  

Venue：横浜（東工大大岡山キャンパス）   Country：Japan  

Event date： 2012.3

Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2012.3

Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2012.3

Presentation type：Oral presentation (general)  

Venue：横浜   Country：Japan  

Event date： 2011.3

Presentation type：Oral presentation (general)  

Venue：横浜（神奈川大学）   Country：Japan  

Event date： 2011.3

Presentation type：Oral presentation (general)  

Venue：横浜（神奈川大学）   Country：Japan  

Event date： 2010.3

Presentation type：Oral presentation (general)  

Venue：大阪（近畿大学）   Country：Japan  

Event date： 2010.3

Presentation type：Oral presentation (general)  

Venue：大阪（近畿大学）   Country：Japan  

Event date： 2010.3

Presentation type：Oral presentation (general)  

Venue：大阪（近畿大学）   Country：Japan  

Event date： 2009.11 - 2011.11

Country：Japan  

Event date： 2009.11

Country：Japan  

Event date： 2009.3

Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2008.12

Country：Japan  

Event date： 2008.3

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：United States  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Presentation type：Oral presentation (general)  

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Asymmetric Aziridination Using Azide Compounds as Nitrene Precursor in the Presence of Robust Ru(salen) Complex

Presentation type：Oral presentation (general)  

Country：Japan  

Asymmetric Baeyer-Villiger Oxidation Using Metallosalen Complex as Catalyst

Presentation type：Symposium, workshop panel (public)  

Venue：淡路夢舞台国際会議場ホール   Country：Japan  

Other Link： http://kuchem.kyoto-u.ac.jp/yugo/www/symposium/index.html

Presentation type：Oral presentation (general)  

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Language：Japanese  

Venue：福岡市東区馬出   Country：Japan  

Event date： 2023.3

Language：English   Presentation type：Oral presentation (general)  

Venue：東京理科大学 野田キャンパス   Country：Japan  

非ヘム型ルテニウム触媒を用いるC–H酸化反応は、系中のカルボン酸の酸性度の向上に伴い反応活性が上昇する傾向が観測されている。そこで、各種カルボン酸の添加挙動の観測を進め、その観測結果からカルボン酸による反応加速効果と配位子交換が進行していることを明らかにした。また、触媒活性の失活過程の一部も明らかとし、その失活過程に基づき、反応性および耐久性を向上させた新規触媒開発を達成した。

Event date： 2022.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

非ヘム型ルテニウム触媒を用いるC–H酸化反応は、系中のカルボン酸の酸性度の向上に伴い反応活性が上昇する傾向が観測されている。そこで、各種カルボン酸の添加挙動の観測を進め、その観測結果からカルボン酸による反応加速効果と配位子交換が進行していることを明らかにした。また、触媒活性の失活過程の一部も明らかとし、その失活過程に基づき、反応性および耐久性を向上させた新規触媒開発を達成した。

Event date： 2021.11

Language：English   Presentation type：Oral presentation (general)  

Country：Italy  

Event date： 2021.10

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2021.10 - 2020.10

Language：Japanese  

Country：Japan  

Event date： 2021.10

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：オンライン   Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2021.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：オンライン   Country：Japan  

Event date： 2020.11

Language：Japanese  

Venue：オンライン   Country：Japan  

水は、地球上に豊富に存在する最も自然環境に優しい酸素源である。しかし、直接使用可能な淡水は地球に存在する水わずか0．01％にしかず、近年の急速な人口増加等により、水の消費量は急激に増加しつつあり、水資源を保全・節約することは極めて重要な課題である。有機合成においても、水は様々な酸素官能基化の酸素源として使用さているが、そのほとんどが、大過剰の水分子が必要であり、省資源および環境汚染等の観点から、水を定量的に扱えるあらたな手法が求められている。一方、本申請手法は、高原子価ヨウ素化合物の可逆的な加水分解反応を活用し、水の酸素原子をほぼ定量的に有機化合物のCH結合へ挿入することが可能である。さらに、本手法により、酸素原子の安定同位体17Oおよび18Oも対応する標識水から定量的に有機化合物へと導入することが可能となった。

Event date： 2019.12

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Event date： 2019.12

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：東大寺総合文化センター（奈良）   Country：Japan  

Event date： 2019.11

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：奈良女子大学（奈良）   Country：Japan  

Event date： 2019.10

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：タワーホール船堀（東京都江戸川区）   Country：Japan  

Event date： 2019.10

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：タワーホール船堀（東京都江戸川区）   Country：Japan  

Event date： 2019.9

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：首都大学東京 南大沢キャンパス（八王子）   Country：Japan  

Event date： 2019.8

Language：English   Presentation type：Oral presentation (general)  

Venue：Yangon   Country：Myanmar  

Event date： 2019.7

Language：English   Presentation type：Symposium, workshop panel (public)  

Venue：シャトレーゼ ガトーキングダム サッポロ（札幌市）   Country：Japan  

Event date： 2019.7

Language：English   Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Other Link： https://confit.atlas.jp/guide/event/naito47/top

Event date： 2019.7

Language：English   Presentation type：Symposium, workshop panel (public)  

Venue：シャトレーゼ ガトーキングダム サッポロ（札幌市）   Country：Japan  

Event date： 2019.7

Language：English   Presentation type：Oral presentation (general)  

Venue：北海道大学学術交流会館（札幌）   Country：Japan  

有機化合物中には、様々な炭素ー水素（C-H)結合が存在する。このC-H結合を自在に目的の位置で目的の立体化学で標的官能基を導入することは現在もなお、限られている。
その様な中、我々は、標的のC–H結合を各種遷移金属錯体を用いることで、高位置かつ高エナンチオ選択的に炭素ー炭素結合、および炭素ー窒素結合へ変換することに成功した。

Event date： 2019.5

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：日本大学理工学部　船橋キャンパス（船橋）   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Symposium, workshop panel (public)  

Venue：日本大学理工学部　船橋キャンパス（船橋）   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：甲南大学岡本キャンパス（神戸）   Country：Japan  

Event date： 2019.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2019.1

Language：English   Presentation type：Symposium, workshop panel (public)  

Venue：Nanyang Technologocal University （Singapore）   Country：Singapore  

Event date： 2014.11

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：熊本市（市民会館崇城大学ホール）   Country：Japan  

Event date： 2013.3 - 2012.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2013.3 - 2012.3

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2011.9 - 2012.9

Venue：大阪   Country：Japan  

Event date： 2008.12

Presentation type：Oral presentation (general)  

Country：Japan  

Event date： 2008.11

Presentation type：Oral presentation (general)  

Venue：天草   Country：Japan  

Presentation type：Oral presentation (general)  

Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Presentation type：Oral presentation (general)  

Venue：fanabashi   Country：Japan  

Presentation type：Symposium, workshop panel (public)  

Country：Japan  

Presentation type：Oral presentation (general)  

Country：Japan  

Presentation type：Oral presentation (general)  

Country：Japan  

Presentation type：Oral presentation (general)  

Country：Japan  

Language：Japanese  

Venue：九州大学馬出キャンパス   Country：Japan  

Language：Japanese   Presentation type：Oral presentation (general)  

Country：Japan  

Language：English   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)  

Language：English   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)  

Language：English   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)  

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Number of participants：100

Type：Peer review 

Number of peer-reviewed articles in foreign language journals：8

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

Type：Competition, symposium, etc. 

公益社団法人　有機合成化学協会　九州山口支部　支部幹事

公益社団法人　有機合成化学協会　有機合成化学協会誌編集協力委員

公益社団法人　有機合成化学協会　有機合成化学協会誌編集協力委員