Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
TATSUYA UCHIDA Last modified date:2021.10.21

Associate Professor / Division for Arts and Science / Division for Experimental Natural Science / Faculty of Arts and Science

1. Doiuchi, Daiki; Uchida, Tatsuya, Catalytic Highly Regioselective C–H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds, Organic Letters, 10.1021/acs.orglett.1c02812, 23, 7301-7305, 2021.09, 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..
2. Masaki Yoshitake, Hiroki Hayashi, Tatsuya Uchida*, Ruthenium-Catalyzed Asymmetric N-Acyl Nitrene Transfer Reaction: Imidation of Sulfide, Organic letters, 10.1021/acs.orglett.0c01373, 22, 10, 4021-4025, 2020.05, (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation..
3. Takuya Oguma, Daiki Doiuchi, Chisaki Fujitomo, Chungsik Kim, Hiroki Hayashi, Tatsuya Uchida, Tsutomu Katsuki, Iron-Catalyzed Asymmetric Inter- and Intramolecular Aerobic Oxidative Dearomatizing Spirocyclization of 2-Naphthols, Asian Journal of Organic Chemistry, 10.1002/ajoc.201900602, 9, 3, 404-415, 2020.03, Highly chemo- and enantioselective inter- and intra-molecular oxidative dearomatizing spirocyclization of 1-alkyl-2-naphthols with O2 as the hydrogen acceptor was achieved using an iron catalyst. In the iron complex 1-catalyzed reaction, 1-methyl-2-naphthols 2 in the presence of phenol derivatives as the nucleophile was selectively oxidized, producing the spirocyclic ketones with good to high enantioselectivities via a tandem strategy. Pre-synthesized 1,1′-methylbis(arenol)s 6 and 7, intermediates of the tandem strategy were also converted to the desired products with chemo- and enantioselectivity..
4. Hiroki Hayashi, Takamasa Ueno, Chungsik Kim, Tatsuya Uchida, Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols, Organic letters, 10.1021/acs.orglett.0c00048, 22, 4, 1469-1474, 2020.02, (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation..
5. Daiki Doiuchi, Tatsuya Nakamura, Hiroki Hayashi, Tatsuya Uchida, Non-Heme-Type Ruthenium Catalyzed Chemo- and Site-Selective C−H Oxidation, Chemistry - An Asian Journal, 10.1002/asia.202000134, 2020.01, 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..
6. Yushu Jin, Yusuke Makida, Tatsuya Uchida, Ryoichi Kuwano, Ruthenium-catalyzed chemo-and enantioselective hydrogenation of isoquinoline carbocycles, Journal of Organic Chemistry, 10.1021/acs.joc.8b00190, 83, 7, 3829-3839, 2018.04, A chemoselective hydrogenation of isoquinoline carbocycles was achieved by using the catalyst prepared from Ru(methallyl)2(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocycle hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization..
7. KIM CHUNG SIK, Takuya Oguma, Chisaki Fujitomo, TATSUYA UCHIDA, Tsutomu Katsuki, Iron-Catalyzed Asymmetric Aerobic Oxidative Dearomatizing Spirocyclization of Methylenebis(arenol)s, Chemistry Letters, 10.1246/cl.160680, 45, 1262-1264, 2016.08, Iron(salan) complexes are efficient catalysis in intramolecular aerobic oxidative dearomatizing spirocyclization of methylenebis(arenol)s, which was prepared from salicyl akdehydes and phenols with simple microwave irradiation. Under the iron-catalyzed aerobic oxidation conditions, methylenebis(arenol)s converted to the corresponding spirocyclic compounds with good to high enantioselectivity (up to 87% ee)..
8. Hirotaka Mizoguchi, TATSUYA UCHIDA, Tsutomu Katsuki, Ruthenium-Catalyzed Oxidative Kinetic Resolution of Unactivated and Activated Secondary Alcohols with Air as the Hydrogen Acceptor at Room Temperature., ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 10.1002/anie.201310426, 53, 3178-3182, 2014.02, Enantiopure alcohols are versatile building blocks for asymmetric synthesis and the kinetic resolution (KR) of racemic alcohols is a reliable method for preparing them. Although many KR methods have been developed, oxidative kinetic resolution (OKR), in which dioxygen is used as the hydrogen acceptor, is the most atom-efficient. Dioxygen is ubiquitous in air, which is abundant and safe to handle. Therefore, OKR with air has been intensively investigated and the OKR of benzylic alcohols was recently achieved by using an Ir catalyst without any adjuvant. However, the OKR of unactivated alcohols remains a challenge. An [(aqua)Ru- (salen)] catalyzed OKR with air as the hydrogen acceptor was developed, in which the aqua ligand is exchanged with alcohol and the Ru complex undergoes single electron transfer to dioxygen and subsequent alcohol oxidation. This OKR can be applied without any adjuvant to activated and unactivated alcohols with good to high enantioselectivity. The unique influence of substrate inhibition on the enantioselectivity of the OKR is also described..
9. Yota Nishioka, TATSUYA UCHIDA, Tsutomu Katsuki, Enantio- and Regioselective Intermolecular Benzylic and Allylic C-H Bond Amination, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 10.1002/anie.201208906, 52, 6, 1739-1742, 2013.01, We designed new ruthenium catalysts that were composed of ruthenium(II) ion, apical CO ligand, and highly enantioselective salen ligand and could for the first time achieve highly enantioselective sulfimidation, aziridination, and C-H amination using azide compounds as the nitrene precursors. Catalytic activity, stereoselectivity, and regioselectivity of the ruthenium catalysts were remarkably improved by an appropriate tuning of salen ligand..
10. Yasuaki Fukunaga, TATSUYA UCHIDA, Yutaro Ito, Tsutomu Katsuki, Ru(CO)-salen-Catalyzed Synthesis of Enantiopure Aziridinyl Ketones and Formal Asymmetric Synthesis of (+)-PD 128907, ORGANIC LETTERS, 10.1021/ol302095r, 14, 17, 4658-4661, 2012.09, Aziridination of vinyl ketones using SESN3 in the presence Ru(CO)-salen complex 1 provides the enantiopure aziridinyl ketones that can serve as useful chiral building blocks. A formal asymmetric synthesis of (þ)-PD 128907 was achieved in an eight-step sequence via aziridination..
11. Shota Koya, Yota Nishioka, Hirotaka Mizoguchi, Tatsuya Uchida, Tsutomu Katsuki, Asymmetric Epoxidation of Conjugated Olefins with Dioxygen, Angew. Chem. Int. Ed., 10.1002/anie.201201848, 51, 33, 8243-8246, 2012.07, A complex situation: Asymmetric epoxidation of conjugated olefins was achieved at room temperature using ruthenium complex 1 as the catalyst and air as the oxidant to give epoxides in up to 95 % ee. When the product was acid sensitive, the reaction was carried out at 0 °C under oxygen..
12. Chungsik Kim, Tatsuya Uchida, Tsutomu Katsuki, Asymmetric olefin aziridination using a newly designed Ru(CO)(salen) complex as the catalyst, Chem. Commun, 10.1039/c2cc32997b, 48, 7188–7190, 2012.04, Highly enantioselective and good to high-yielding aziridination of conjugated and non-conjugated terminal olefins and cyclic olefins was achieved using a newly designed Ru(CO)(salen) complex as the catalyst in the presence of SESN3 under mild conditions..
13. Ryo Irie, Akihiro Tanoue, Suguru Urakawa, Tatsushi Imahori, Kazunobu Igawa, Taisuke Matsumoto, Katsuhiko Tomooka, Shinsuke Kikuta, Tatsuya Uchida, Tsutomu Katsuki, Synthesis and stereochemical behavior of a new chiral oxa[7]heterohelicene, Chemistry Letters, 10.1246/cl.2011.1343, 40, 12, 1343-1345, 2011.11, A new chiral oxa[7]heterohelicene 1b was synthesized by catalytic aerobic-oxidative tandem cyclization of the o-phenylene-linked bis(2-naphthol) derivative 3 with palladium acetate in dimethyl sulfoxide. Optical resolution of 1b was possible on chiral HPLC, but it was found stereochemically rather unstable at ambient temperature. Kinetic analysis and DFT calculation for the dynamics of racemization of 1b were also disclosed..
14. Masami Ichinose, Hidehiro Suematsu, Yoichi Yasutomi, Yota Nishioka, Tatsuya Uchida, and Tsutomu Katsuki, Enantioselective Intramolecular Benzylic CーH Bond Amination:
Efficient Synthesis of Optically Active Benzosultams, Angew. Chem. Int. Ed, 10.1002/anie.201101801, 50, 9884-9887, 2011.09.
15. Tanaka, H., Nishikawa, H., Uchida, T. & Katsuki, T., , Photopromoted Ru-Catalyzed Asymmetric Aerobic Sulfide Oxidation and Epoxidation Using Water as a Proton Transfer Mediator., J. Am. Chem. Soc, 10.1021/ja104184r, 132, 34, 12034-12041, 2010.05, 著者等は、光学活性なルテニウム(ニトロシル)サレン錯体が、室温、常圧の温和な条件下で還元剤を用いること無しに、分子状酸素を酸化剤とするオレフィンの不斉エポキシ化、スルフィドの不斉スルホキシ化に成功した。可視光照射条件下において、錯体2を触媒とすることで不斉スルホキシ化が最高98% eeのエナンチオ選択性にて、また錯体3を用いることにて不斉エポキシ化が76-92% eeの不斉収率にて目的とする酸化生成物が得られた。
16. Hirotaka Mizoguchi, Tatsuya Uchida, Kohichi Ishida, Tsutomu Katsuki, Ru(PPh3)(OH)-salen complex
a designer catalyst for chemoselective aerobic oxidation of primary alcohols, Tetrahedron Letters, 10.1016/j.tetlet.2009.02.169, 50, 26, 3432-3435, 2009.07, Based on the analysis of the mechanism of aerobic oxidation of alcohols using Ru(NO)-salen catalyst, we designed a new complex, Ru(PPh3)(OH)-salen 3, which was proved to be an excellent catalyst for chemoselective aerobic oxidation of primary alcohols to the aldehydes in the presence of secondary alcohols under ambient and non-irradiated conditions. Complex 3 was also successfully applied to the oxidation of 1-phenyl-1,n-diols to the lactols or the n-hydroxy aldehyde. It is of note that selective oxidation of primary alcohols was achieved even in the presence of activated secondary alcohols..
17. Mizoguchi Takahiro, Ishida Koichi, Uchida Tatsuya, Katsuki Tsutomu , Ru-salen complex catalyzed chemoselective aerobic oxidation of primary alcohols to aldehydes, Tetrahedron Letters, 2009.06.
18. Tatsuya Uchida, Tstomu Katsuki, Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation, Tetrahedron Letters, 2009.06.
19. Hidehiro Suematsu, Shigefumi Kanchiku, Tatsuya Uchida, Tsutomu Katsuki, Construction of aryliridium-salen complexes
Enantio- and cis-selective cyclopropanation of conjugated and nonconjugated olefins, Journal of the American Chemical Society, 10.1021/ja802561t, 130, 31, 10327-10337, 2008.08, Two stable and optically active iridium-salen complexes were synthesized by introducing a tolyl or phenyl ligand at the apical position, respectively, via the SEAr mechanism, and they were found to be efficient catalysts for cis-selective asymmetric cyclopropanation. The scope of the cyclopropanation was wide, and the reactions of not only conjugated mono-, di-, and trisubstituted olefins but also nonconjugated terminal olefins proceeded with high enantio- and cis-selectivity, even in the presence of a functional group such as an ether or ester. The utility of this cyclopropanation was demonstrated by a short step synthesis of 8-[(1R,2S)-2-hexylcyclopropyl]octanoate, isolated from Escherichia coli B-ATCC 11303, using the reaction as the key step..
20. Satomi Eno, Hiromichi Egami, Tatsuya Uchida, Tsutomu Katsuki, Asymmetric hetero Diels-Alder reaction catalyzed by chromium complexes of heterogeneously hybridized salen/salan ligands, Chemistry Letters, 10.1246/cl.2008.632, 37, 6, 632-633, 2008.06, Various heterogeneously or homogeneously hybridized salen/salan ligands were synthesized, and study of hetero Diels-Alder reactions using their chromium complexes as catalysts revealed that a well-designed heterogeneously hybridized ligand serves as a chiral auxiliary as efficiently as the homogeneously hybridized ligand and its chromium complex has high catalytic activity..
21. Hidekazu Fujita, Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki, Asymmetric sulfimidation with cis-β Ru(salalen)CO2 complexes as catalyst, Chemistry Letters, 10.1246/cl.2007.1092, 36, 9, 1092-1093, 2007.09, 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..
22. Y. Nakamura, H. Egami, K. Matsumoto, T. Uchida, T. Katsuki, Aerobic Oxidative Kinetic Resolution of Racemic Alcohols with Bidentate Ligand-Binding Ru(salen) Complex as Catalyst, Tetrahedron, 63, 6383-6387 (2007)., 2007.07.
23. Hirotoshi Kawabata, Kazufumi Omura, Tatsuya Uchida, Tsutomu Katsuki, Construction of robust ruthenium(salen)(CO) complexes and asymmetric aziridination with nitrene precursors in the form of azide compounds that bear easily removable N-sulfonyl groups, Chemistry - An Asian Journal, 10.1002/asia.200600363, 2, 2, 248-256, 2007.07, We synthesized new Ru-(salen)(CO) complexes of high durability and achieved aziridination with good to excellent enantiosclectivity by using azide compounds that contain an easily removable N-sulfonyl group, such as the 2-(trimethylsilyl)ethancsulfonyl group, as a nitrene precursor. Aziridination of less-reactive α,β-unsaturated esters (and amides) proceeded with excellent enantioselectivities, from which it is inferred that an electrophilic species is the active species of this reaction. The present asymmetric aziridination provides a useful tool for introducing optically active nonprotected amine groups..
24. Shigefumi Kanchiku, Hidehiro Suematsu, Kazuhiro Matsumoto, Tatsuya Uchida, Tsutomu Katsuki, Construction of an aryliridium-salen complex for highly cis- and enantioselective cyclopropanations, Angewandte Chemie - International Edition, 10.1002/anie.200604385, 46, 21, 3889-3891, 2007.06, (Chemical Equation Presented) Ringing the changes: Iridium(lll)-salen complexes 1 bearing a σ-coordinated aryl ligand (L = CH3C 6H4, C6H5) at the apical position are found to efficiently catalyze the cis- and enantioselective cyclopropanation of mono- and disubstituted olefins (see scheme)..
25. Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Optically active metallosalen complexes as catalysts for atom-efficient asymmetric reactions, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 63, 5, 478-491, 63卷、5号、478-491, 2005.05.
26. Watanabe Akira, Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: Stereospecific synthesis of abnormal and normal lactones, PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 10.1073/pnas.0306992101, 101, 16, 5737-5742, 101卷、19号、5737−5742, 2004.04.
27. Matsumoto Kazuhiro、Watanabe Akira、Uchida Tatsuya、Ogi Kayoko、Katsuki Tsutomu, Construction of a new asymmetric reaction site: asymmetric 1,4-addition of thiol using pentagonal bipyramidal Hf(salen) complex as catalyst, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2004.01.095, 45, 11, 2385-2388, 45巻11号、p. 2385-2388, 2004.03.
28. Omura Kazuhumi, Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Design of a robust Ru(salen) complex: aziridination with improved turnover number using N-arylsulfonyl azides as precursors, CHEMICAL COMMUNICATIONS, 10.1039/b407693a, 18, 2060-2061, 18号、2060-2061, 2004.01.
29. Uchida Tatsuya, Tamura Yuusuke, Katsuki Tsutomu, Mechanism of asymmetric sulfimidation with N-alkoxycarbonyl azide in the presence of (OC)Ru(salen) complex, TETRAHEDRON LETTERS, 10.1016/j.tetlet.2003.08.108, 44, 43, 7965-7968, 44巻43号、p. 7965-7968, 2003.10.
30. Omura Kazuhumi, Murakami Masakazu, Uchida Tatsuya, Katsuki Tsutomu, Enantioselective aziridination and amination using p-toluenesulfonyl azide in the presence of Ru(salen)(CO) complex, CHEMISTRY LETTERS, 32, 4, 354-355, 32巻4号、p. 354-355, 2003.04.
31. Saha Biswajit, Uchida Tatsuya, Katsuki Tsutomu, Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: structural tuning of salen ligand, TETRAHEDRON-ASYMMETRY, 10.1016/S0957-4166(03)00167-8, 14, 7, 823-836, 14巻7号、p. 823-836, 2003.04.
32. Tamura Yuusuke, Uchida Tatsuya, Katsuki Tsutomu, Highly enantioselective (OC)Ru(salen)-catalyzed sulfimidation using N-alkoxycarbonyl azide as nitrene precursor, TETRAHEDRON LETTERS, 10.1016/S0040-4039(03)00609-9, 44, 16, 3301-3303, 44巻16号、p. 3301-3303, 2003.04.
33. Kazufumi Omura, Masakazu Murakami, Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki, Enantioselective aziridination and amination using p-toluenesulfonyl azide in the presence of Ru(salen)(CO) complex, Chemistry Letters, 10.1246/cl.2003.354, 32, 4, 354-355, 2003.04, (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..
34. Murakami Masakazu, Uchida Tatsuya, Saito Bunnai, Katsuki Tsutomu, Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement, CHIRALITY, 10.1002/chir.10156, 15, 2, 116-123, 15巻2号、p.116-123, 2003.02.
35. Saha Biswajit, Uchida Tatsuya, Katsuki Tsutomu, Highly enantioselective intramolecular cyclopropanation of alkenyl diazo ketones using Ru(salen) as catalyst, CHEMISTRY LETTERS, 10.1246/cl.2002.846, 8, 846-847, 8号、p.846-847, 2002.08.
36. (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..
37. Uchida Tatsuya, Katsuki Tsutomu, Ito Katsuji, Akashi Sumie, Ishii Ayako, Kuroda Tomomi, New asymmetric catalysis by (Salen)cobalt(III) complexes (Salen=[Bis(salicylidene)ethylenediaminato]={{2,2'-[ethane-1,2-diyl]bis[(nitrilo-kappa N)methylidyne]bis[phenolato-kappa O]}(2-)}) of cis-beta-structure: Enantioselective Baeyer-Villiger oxidation of prochiral cyclobutanones, HELVETICA CHIMICA ACTA, 10.1002/1522-2675(200210)85:10<3078::AID-HLCA3078>3.0.CO;2-1, 85, 10, 3078-3089, 85巻10号、p.3078-3089, 2002.01.
38. Murakami Masakazu, Uchida Tatsuya, Katsuki Tsutomu, Ru(salen)-catalyzed asymmetric sulfimidation using arylsulfonyl azide, TETRAHEDRON LETTERS, 10.1016/S0040-4039(01)01448-4, 42, 40, 7071-7074, 42巻40号、p.7071-7074, 2001.10.
39. 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..
40. Uchida Tatsuya, Saha Biswajit, Katsuki Tsutomu, Co(II)-salen-catalyzed asymmetric intramolecular cyclopropanation, TETRAHEDRON LETTERS, 10.1016/S0040-4039(01)00218-0, 42, 13, 2521-2524, 42巻、13号、p.2521-2524, 2001.03.
41. K. Ito, R. Kashiwagi, S. Hayashi, T. Uchida, T. Katsuki, 2-(Phosphinoaryl)pyridine ligand (2)
Asymmetric allylic alkylation of 2-cycloalkenyl carboxylate, Synlett, 2, 284-286, 2001.02, Palladium complex of 2-(phosphinoaryl)pyridine 1b, which is an effective catalyst for asymmetric allylic alkylation (denoted as AAA) of acyclic alkenyl carboxylate, was also found to be a highly effective catalyst for AAA of cyclic alkenyl carboxylate: high enantioselectivities of 87% ee and 94% ee were achieved in the reactions of 2-cyclohexenyl and 2-cycloheptenyl pivalates, respectively..
42. Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, cis- and enantio-selective cyclopropanation with chiral (ON+)Ru-salen complex as a catalyst, TETRAHEDRON, 10.1016/S0040-4020(00)00273-8, 56, 22, 3501-3509, 55巻、22号、p.3501-3509, 2000.05.
43. Niimi Tatsuo, Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Co(II)-salen-catalyzed highly cis- and enantioselective cyclopropanation, TETRAHEDRON LETTERS, 10.1016/S0040-4039(00)00433-0, 41, 19, 3647-3651, 41巻、 19号、p. 3647-3651, 2000.05.
44. Masutani Kouta, Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Catalytic asymmetric and chemoselective aerobic oxidation: kinetic resolution of sec-alcohols, TETRAHEDRON LETTERS, 10.1016/S0040-4039(00)00787-5, 41, 26, 5119-5123, 41巻、26号、p.5119-5123, 2000.06.
45. 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..
46. Saha Biswajit, Uchida Tatsuya, Katsuki Tsutomu, Intramolecular asymmetric cyclopropanation with (nitroso)(salen)-ruthenium(II) complexes as catalysts, SYNLETT, 1, 114-116, 1号、p.114-116, 2001.01.
47. Tatsuo Niimi, Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki, Highly Enantioselective Cyclopropanation with Co(II)-Salen Complexes
Control of cis- and trans-Selectivity by Rational Ligand-Design, Advanced Synthesis and Catalysis, 343, 1, 79-88, 2001.01, Cyclopropanation of styrene derivatives with alkyl α-diazoacetate in the presence of the second-generation (salen)cobalt(II) complex 6 proceeded with excellent cis- and enantioselectivity. On the other hand, the cyclopropanation in the presence of complex 14 which was designed on the basis of the mechanism of asymmetric induction by complex 6 showed good trans- and excellent enantio-selectivity..
48. Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki, Chiral (ON)Ru-salen catalyzed cyclopropanation
High cis- and enantio-selectivity, Synlett, 10.1055/s-1999-2782, 7, 1163-1165, 1999.01, (R,R)-(ON+)(Salen)ruthenium(II) complex 2 was found to be an effective catalyst for cis-selective asymmetric cyclopropanation (up to 89% ee) which was performed under sunlight coming through a window or incandescent light. Furthermore, (R,R)-(ON+)(hydroxo)-(salen)ruthenium(II) complex 5 was also found to show good cis- and enantio-selectivities (up to 92% ee) in the reaction in the dark..
49. Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki, Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru- salen complex
Solubility dependent enantioface selection, Synlett, 10.1055/s-1999-2955, 11, 1793-1795, 1999.01, The reaction of styrene and t-butyl α-diazoacetate in the presence of (R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandescent light in THF gave the corresponding (IS,2R)- cyclopropanecarboxylate with high stereoselectivity of 99% ee (cis: trans = 96:4), while the same reaction in hexane gave the enantiomeric (1R,2S)- cyclopropanecarboxylate preferentially (83% ee, cis: trans = 68:32)..