TOPIC: Bifunctional, Dual, and Integrated Organocatalysis for Asymmetric Reactions
SPEAKER: Prof. Yoshiji Takemoto，Graduate School of Pharmaceutical Sciences，Kyoto University
TIME:May 3 (Tuesday) PM15:30
LOCATION: Room 528, Chemistry Building A (化学A楼528演讲厅)
INVITER: Prof. Wanbin Zhang(张万斌教授)
Graduate School of Pharmaceutical Sciences
Yoshida, Sakyo-ku, Kyoto 606-8501, Japan
home page: http://www.pharm.kyoto-u.ac.jp/orgchem/
Osaka University, Suita, Osaka
Ph.D., Pharmaceutical Sciences, March 1988
Dissertation Title: "Total Synthesis of Biologically Active Spiro[4.5]decane Sesquiterpines"
Osaka University, Suita, Osaka
B.S., Pharmaceutical Sciences, March 1983
Professor (April, 2000 to present)
Graduate School of Pharmaceutical Sciences, Kyoto University
Research areas include: a) design and creation of innovative artificial catalysts for asymmetric reactions directing to green chemistry, b) development of new metal-catalyzed reactions, and c) total synthesis of naturally occurring compounds that are of biological importance.
Associate Professor (February, 1998 to March, 2000)
Graduate School of Pharmaceutical Sciences, Kyoto University
Assistant Professor (April, 1990 to January, 1998)
Graduate School of Pharmaceutical Sciences, Osaka University
Post-Doctoral Fellow (April, 1989 to March, 1990)
Sagami Chemical Research Center, Kanagawa, Japan
Conducted investigations concerning stereoselective synthesis of statines and â-lactams.
Advisor: Dr. Shiro Terashima
Post-Doctoral Fellow (April, 1988 to March, 1989)
Florida State University, Tallahassee, Florida
Conducted investigations concerning total synthesis of Taxol.
Advisor: Professor R. A. Holton
HONORS and AWARDS:
Takeda Award in Synthetic Organic Chemistry, Japan (1992)
The Pharmaceutical Society of Japan Kinki Branch Award for Young Scientists (1994)
Thomson Research Front Award (2007)
The PSJ (the Pharmaceutical Society of Japan) Award for Divisional Scientific Promotions (2008)
The Pharmaceutical Society of Japan
The Chemical Society of Japan
The Society of Synthetic Organic Chemistry, Japan
American Chemical Society
International Society of Heterocyclic Chemistry
(1) Asymmetric Synthesis of Drug Candidates with Organocatalysts
1. Azuma, T.; Murata, A.; Kobayashi, Y.; Inokuma, T.; Takemoto, Y., A Dual Arylboronic
Acid–Aminothiourea Catalytic System for the Asymmetric Intramolecular Hetero-Michael Reaction of α,β-Unsaturated Carboxylic Acids. Org. Lett. 2014, 16, (16), 4256-4259.
2. Tsuji, N.; Kobayashi, Y.; Takemoto, Y., Electrophilic iodine(I) compounds induced semipinacol rearrangement via C–X bond cleavage. Chem. Commun. 2014, 50, (89), 13691-13694.
3. Sakamoto, S.; Kazumi, N.; Kobayashi, Y.; Tsukano, C.; Takemoto, Y., Asymmetric Synthesis of Trisubstituted Oxazolidinones by the Thiourea-Catalyzed Aldol Reaction of 2‑Isocyanatomalonate Diester, Org. Lett. 2014, 16, 4758−4761.
4. Azuma, T.; Kobayashi, Y.; Sakata, K.; Sasamori, T.; Tokitoh, N.; Takemoto, Y., Synthesis and Characterization of Binary-Complex Models of Ureas and 1,3-Dicarbonyl Compounds: Deeper Insights into Reaction Mechanisms Using Snap-Shot Structural Analysis. J. Org. Chem. 2014, 79, (4),
5. Kobayashi, Y.; Taniguchi, Y.; Hayama, N.; Inokuma, T.; Takemoto, Y., A Highly Powerful Hydrogen-bond-donor Organocatalyst for the Enantioselective Oxa-Michael Reaction of Unactivated α,β-Unsaturated Amides and Esters. Angew. Chem. Int. Ed. 2013, 52, (42), 11114-11118.
6. Yamaoka, Y.; Miyabe, H.; Takemoto, Y., Catalytic Enantioselective Petasis-type Reaction of Quinolines Catalyzed by a Newly Designed Thiourea Catalyst. J. Am. Chem. Soc. 2007, 129, (21), 6686-6687.
7. Inokuma, T.; Hoashi, Y.; Takemoto, Y., Thiourea-Catalyzed Asymmetric Michael Addition of Activated Methylene Compounds to a,b-Unsaturated Imides: Dual Activation of Imide by Intra- and Intermolecular Hydrogen-bonding. J. Am. Chem. Soc. 2006, 128, (29), 9413-9419.
8. Hoashi, Y.; Okino, T.; Takemoto, Y., Enantioselective Michael Addition to a,b-Unsaturated Imides Catalyzed by a Bifunctional Organocatalyst. Angew. Chem. Int. Ed. 2005, 44, (26), 4032-4035.
9. Okino, T.; Hoashi, Y.; Furukawa, T.; Xuenong, X.; Takemoto., Y., Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea. J. Am. Chem. Soc. 2005, 127, (1), 119-125.
10. Okino, T.; Hoashi, Y.; Takemoto, Y., Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts. J. Am. Chem. Soc. 2003, 125, (42), 12672-12673.
(2) Development of Metal-Catalyzed Reactions for Nitrogen-Containing Heterocycles. 1. Tsukano, C.; Muto, N.; Enkhtaivan, I.; Takemoto, Y., Synthesis of Pyrrolophenanthridine Alkaloids Based on C(sp3)-H and C(sp2)-H Functionalization Reactions. Chem. Asian J. 2014, 9, (9), 2628–2634.
2. Nanjo, T.; Tsukano, C.; Takemoto, Y., Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)-H Activation: Concise Synthesis of the Indole Derivatives. Org. Lett. 2012, 14, (16), 4270-4273.
3. Tsukano, C.; Okuno, M.; Takemoto, Y., Palladium-Catalyzed Amidation by Chemoselective C(sp3)-H Activation: Concise Route to Oxindoles Using a Carbamoyl Chloride Precursor. Angew. Chem. Int. Ed. 2012, 51, (11), 2763-2766.
4. Hande, S. M.; Nakajima, M.; Kamisaki, H.; Tsukano, C.; Takemoto, Y., Flexible Strategy for Syntheses of Spirooxindoles using Palladium-Catalyzed Carbosilylation and Sakurai-Type Cyclization. Org. Lett. 2011, 13, (7), 1828-1831.
5. Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y., In(OTf)3-catalyzed tandem nucleophilic addition and cyclization of ortho-alkynylarylaldimines to 1,2-dihydroisoquinolines. Angew. Chem. Int. Ed. 2006, 45, (23), 3822-3825.
(3) Total Synthesis of Natural Products and Others
1. Nakamura, H.; Tsukano, C.; Yasui, M.; Yokouchi, S.; Igarashi, M.; Takemoto*, Y., Total Synthesis of (–)-Caprazamycin A**. Angew. Chem. Int. Ed. 2015, 54, (10), 3136 –3139.
2. Suetsugu, S.; Nishiguchi, H.; Tsukano, C.; Takemoto*, Y., Asymmetric Synthesis of (−)-Aurantioclavine via Palladium-Catalyzed Intramolecular Allylic Amination. Org. Lett. 2014, 16, (2), 996−999.
3. Ishida, T.; Ikota, H.; Kurahashi, K.; Tsukano, C.; Takemoto, Y., Dearomatizing Conjugate Addition to Quinolinyl Amidines for the Synthesis of Dehaloperophoramidine via Tandem Arylation and Allylation. Angew. Chem. Int. Ed. 2013, 52, (39), 10204-10207.
4. Shindoh, N.; Kitaura, K.; Takemoto, Y.; Takasu, K., Catalyst-Controlled Torquoselectivity Switch in the 4π Ring-Opening Reaction of 2-Amino-2-azetines Giving β-Substituted α,β-Unsaturated Amidines. J. Am. Chem. Soc. 2011, 133, (22), 8470-8473.
1. 28th Seminar of Organic Reaction, Kyoto, August 3, 2002.
2. Seminar of Heteroatom division, Hyogo, October 25, 2002.
3. 4th Exchange Forum for Pharmaceutical Research, Osaka, March 8, 2003
4. Bayer Yakuhin, Ltd., Kyoto, May 13, 2003
5. Korea-Japan Young Scientists Joint Symposium, Seoul, July 28-29, 2003.
6. 21st COE Symposium, Kyoto, March 11, 2004.
7. Daiichi Suntory Pharm Co., Ltd., September 9, 2004.
8. Symposium for Optically Active Compounds, Tokyo, October 29, 2004.
9. Seminar for Synthetic Organic Chemistry, Tokyo, November 10-11, 2004.
10. Takeda Pharmaceutical Company Limited, March 18, 2005.
11. The Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 29-31, 2005.
12. 10th PharmaScience Forum, Saporo, October 3, 2005.
13. The Pacifichem 2005, Hawaii, December 15-20, 2005.
14. The 16th International Conference on Organic Synthesis（Merida, Yucatan, Mexico）11-15 June 2006.
15. 45th Tutzing Symposion Organocatalysis (Tutzing), Oct 8-11 2006.
16. International Asymmetric Organocatalytic Conference (Ohtsu), May 28-29 2007.
17. The Fourth International Symposium on Integrated Synthesis (Hikone), September 23–24, 2007.
18. Agenda 2nd Flash Conference (Evora, Portugal), October 29–31, 2007.
19. First Japan-Singapore Bilateral Symposium on Catalysis (Singapore), January 6–9, 2008.
20. UK/Japan Symposium on Asymmetric Catalysis (Kyoto), December 8–9, 2008.
21. Novel Chiral Chemistries Japan（NCCJ）2009 (Tokyo), April 18-19, 2009.
22. F. Hoffmann-La Roche Ltd (Basel, Switzerland), July 21, 2009.
23. Sanofi aventis (Montpellier, France), July 23, 2009.
24. Novartis Pharma AG (Basel, Switserland), July 24, 2009 .
25. Johnson-Johnson (Beerse, Belgium), July 31, 2009.
26. Synthetic Organic Chemistry Seminar (Osaka), Oct 28, 2009.
27. Sumitomo Chemical Co., Ltd. (Osaka), Feb 1, 2010.
28. The 130 Annual Meeting of the Pharmaceutical Society of Japan (Okayama), March 28, 2010.
29. Kanazawa University (Kanazawa), June 21, 2010.
30. International Symposium on Organocatalysis (Mulheim an der Ruhr, Germany), July 15, 2010.
31. 35th Kanto Branch Academic Seminar of the Pharmaceutical Society of Japan (Tokyo), Nov 13, 2010.
32. Pacifichem 2010 (Hawaii, USA), Dec 17, 2010.
33. 1st Germany-Japan Organocatalytic Symposium (Kyoto) Oct 14, 2011.
34. Mitsui Chemicals Agro, Inc. (Chiba), March 6, 2012.
35. Kanto Branch Symposium of the Chemical Society of Japan (Tokyo), Aug 31, 2012.
36. The 6th Takeda Science Foundation Symposium on PharmaSciences “How Fascinating the Synthetic Organic Chemistry is!”(Osaka) Sep 13-14, 2012.
37. International Conference “Catalysis in Organic Synthesis”, (Moscow, Russia) Sep 15-20, 2012.
38. Bristol-Kyoto Organic Synthesis Workshop in Kyoto, (Kyoto, Japan), November 16-17, 2012.
39. Japan-USA Organocatalytic Symposium in Hawaii (Hawaii, USA), Dec 15-19, 2012.
40. Advanced Molecular Transformations by Organocatalysts: 1st International Conference (Otsu Prince Hotel, Otsu, Japan) May 27-28, 2013.
41. Aix-Marseille University, iSm2, France (Oct. 8, 2013).
42. Caen University, ICMT, France (Oct. 11, 2013).
43. University of Rouen, IRCOF, France (Oct. 16, 2013).
44. University of Strasbourg, ECPM, France (Oct. 18, 2013).
45. Nagasaki University, Graduate School of Pharmaceutical Sciences (Nov. 14-15, 2013).
46. Jawaharlal Nehru Centre for Advanced Scientific Research, New Chemistry Unit (Jan. 27, 2014).
47. Indian Institute of Science, Dep. of Org. Chem. (Jan. 28, 2014).
48. Jubilant Biosys (Jan. 28, 2014).
49. Indian Institute of Technology Bombay, Dep. of Chem. (Jan. 29, 2014).
50. Indo Japanese Conference on Process Chemistry R & D 2014 (Hotel Ramada Plaza Palm Grove, Mumbai, India) Jan 30, 2014, Asymmetric Reactions Using Bifunctional Hydrogen-Bond-Donor Catalysts, Yoshiji Takemoto (invited lecture).
51. Organocatalysis Joint Symposium (Sapporo, Hokkaido), Jun. 20-21, 2014 (invited lecture).
52. Kyusyu University, Graduate School of Science (Jul. 24, 2014).
53. Osaka City University, Graduate School of Science (Sep. 25, 2014).
54. Sungkyunkwan University, Department of Chemistry (Nov. 3, 2014).
55. Ewha Womans University, Department of Chemistry and Nano Sciences (Nov. 4, 2014).
56. Advanced Molecular Transformations by Organocatalysts: 2nd International Conference (Tokyo, Japan) Nov. 21, 2014, Asymmetric hetero-Michael reaction of a,b-unsaturated carboxylic acid derivatives, Yoshiji Takemoto (invited lecture).
57. The 13th Eurasia Conference in Chemical Sciences (Indian Institute of Science, Bangalore, India) Dec. 14-18, 2014, Asymmetric hetero-Michael reaction of a,b-unsaturated carboxylic acid derivatives, Yoshiji Takemoto (invited lecture).
58. Nagoya University, Graduate School of Enginering (Apr. 15, 2015).
59. Tanabe-Mitsumishi Pharm. (Jun. 18, 2015)
60. The chemistry of organocatalysts (Chateraise Gateaux Kingdom Sapporo, Sapporo, Hokkaido) Jul. 6-9,
2015, Asymmetric catalysis for the Michael addition of α,β-unsaturated carboxylic acids, Yoshiji Takemoto (invited lecture)
1. Manufacture of 4-amino-3-hydroxypentanoic acid derivatives. Terajima, Y. Takemoto, Y. Ito & M. Matsumoto, Jpn. Kokai Tokkyo Koho, JP 03123765 (1991).
2. Preparation of (3R)-2-azetidinone derivatives. Terajima, Y. Ito, Y. Takemoto & Y. Kobayashi, Jpn. Kokai Tokkyo Koho, JP 03284665 (1991).
3. Preparation of 7-amino-3-chloromethyl-3-cephem-4-carboxylic acid esters as intermediates for cephalosporin antibiotics. Terajima, Y. Takemoto, T. Kato, S. Tachibana & Y. Konishi, Jpn. Kokai Tokkyo Koho, JP 04066584 (1992).
4. Preparation of (4R,5R)-4-[(S)-(1-amino-2-cyclohexyl)ethyl]-1,3-dioxolane derivatives. Terajima, Y. Ito, M. Sugiura, Y. Takemoto & Y. Kobayashi, Jpn. Kokai Tokkyo Koho, JP 04046174 (1992).
5. Preparation of thiadiazoyl acid chlorides as intermediates for cephalosporin antibiotics. Terajima, T. Kato, Y. Takemoto, S. Tachibana & Y. Konishi, Jpn. Kokai Tokkyo Koho, JP 04128277 (1992).
6. Ionic Liquid OsO4, R. Yanada, Y. Takemoto, 2002-217728、Jul 26, 2002. 7. Chiral Thiourea Catalyst and Preparation of Chiral Compounds Using Thiourea-Catalyzed Michael Addition, 2003-189096, Jun 30, 2003 (WO/2005/000803).
8. Preparation of Chiral Amines, 2003-420105, Dec 30, 2003 (WO/2005/058805).
9. Preparation of Chiral Hydrazine Compounds, 2005-054799, Feb 28, 2005.
10. Compound having hetero ring skeleton as asymmetric catalyst, and process for the preparation of optically active compound thereby, PCT/JP2010/056463, Apr 9, 2010 (WO/2010/117064).
11. Preparation of Chiral isoxazolidines, 2012-206320, Sep 19, 2012 (WO2014/046172).