Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
TATSUYA UCHIDA Last modified date:2018.06.14

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


Papers
1. KIM CHUNG SIK, Takuya Oguma, Chisaki Fujitomo, TATSUYA UCHIDA, Tsutomu Katsuki, Iron-Catalyzed Asymmetric Aerobic Oxidative Dearomatizing Spirocyclization of Methylenebis(arenol)s, The Chemical Society of Japan, 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)..
2. 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..
3. 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..
4. 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..
5. 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..
6. 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..
7. 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.
8. 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。
本反応では、反応系中に存在する水分子が、ルテニウムイオンに配位し、プロトン供給源として分子状酸素活性化の一翼を担い、また、消費された水は反応サイクル中で再生するものと考えられる。.
9. Tatsuya Uchida, Tstomu Katsuki, Construction of a new type of chiral bidentate NHC ligands: copper-catalyzed asymmetric conjugate alkylation, Tetrahedron Letters, 2009.06.
10. Mizoguchi Takahiro, Ishida Koichi, Uchida Tatsuya, Katsuki Tsutomu , Ru-salen complex catalyzed chemoselective aerobic oxidation of primary alcohols to aldehydes, Tetrahedron Letters, 2009.06.
11. H. Suematsu, S. Kanchiku, T. Uchida, T. Katsuki, Construction of Aryliridium-salen Complexes: Enantio- and Cis-Selective Cyclopropanation of Conjugated and Nonconjugated Olefins, J. Am. Chem. Soc, 130, 10327-10337, 2008.12.
12. S. Eno, H. Egami, T. Uchida, T. Katsuki, Asymmetric hetero Diels-Alder reaction catalyzed by chromium complexes of heterogeneously hybridized salen/salan ligands, Chenistry Letters, 37, 632-633, 2008.06.
13. 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.
14. H. Fujita, T. Uchida, R. Irie and T. Katsuki, Asymmetric sulfimidation with cis-b Ru(salalen)(CO)2 complexes as catalyst, Chemistry Letters, 36(9), 1092-1093 (2007)., 2007.09.
15. S. Kanchiku, H. Suematsu, K. Matsumoto, T. Uchida, T. Katsuki, Construction of an Aryliridium-Salen Complex for Highly cis- and Enantioselective Cyclopropanations, Angew. Chem. Int. Ed, early view , 2007.04.
16. H. Kawabata, K. Omura, T. Uchida, T. 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, 2(2), 248-256, 2007.04.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. (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..
28. 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.
29. 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.
30. 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..
31. 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.
32. 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.
33. 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..
34. Cyclopropanation of styrene derivatives with alkyl alpha -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 enantioselectivity..
35. 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.
36. 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.
37. 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.
38. Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru-salen complex: Solubility dependent enantioface selection, SYNLETT, 11, 1793-1795, p.1793-1795, 1999.11.
39. Uchida Tatsuya, Irie Ryo, Katsuki Tsutomu, Chiral (ON)Ru-salen-catalyzed cyclopropanation. High cis- and enantio-selectivity., Synlett, 7, 1163-1165, p. 1163-1165., 1999.07.