Faculty Information, Institute for Chemical Research, Kyoto University     [ English | Japanese ]


KAWABATA, Takeo

Division of Synthetic Chemistry - Fine Organic Synthesis -
(Laboratory in the Faculty of pharmaceufical Sciences)
Professor
Doctor Pharmaceutical Science

E-mail: kawabata@scl.kyoto-u.ac.jp
Tel: 0774-38-3190
Fax: 0774-38-3197
Academic career
    1983.3 Graduated from Dr. Course, Kyoto University
    1983.11 D. Pharm. Sc, Kyoto University
    1983.11-1985.9 Postdoctoral Fellow, Indiana University, USA
    1985.11-1989.3 Researcher, Sagami Chemical Research Center
    1989.4-1998. 5 Assistant Professor, Kyoto University, Institute for Chemical Research
    1998.6- Associate Professor, Kyoto University, Institute for Chemical Research
    2004.4- Professor, Kyoto University, Institute for Chemical Research
Research field
    Synthetic Organic Chemistry, Asymmetric Synthesis
Current research
  1. Nucleophilic Catalysis in Selective Reactions
  2. Asymmetric Synthesis based on Dynamic Chirality of Enolates
  3. Synthesis of Biologically Active Natural Products
Selected publications
  1. Kawabata T, Chen J, Suzuki H, Fuji K , Stereochemical Study on ¦Á-Alkylation of ¦Â-Branched ¦Á-Amino Acid Derivatives via Memory of Chirality. Synthesis 8, 1368-1377 (2005)
  2. Tsubaki K, Tanima D, Mohammad N, Kusumoto T, Fuji K, Kawabata T, Visual Enantiomeric Recognition of Amino Acid Derivatives in Protic Solvents. J.Org. Chem 70, 4609-4616 (2005)
  3. Kawabata T, Majumdar S, Tsubaki K, Monguchi D, Memory of Chirality in Intramolecular Conjugate Addition of Enolates: A Novel Access to Nitrogen Heterocycles with Contiguous Quaternary and Tertiary Stereocenter. Org.Biomol.Chem 3, 1609-1611 (2005)
  4. Tsubaki K, Kusumoto T, Hayashi N, Tanima D, Fuji K, Kawabata T, Convenient Preparation of Optically Active N,N-Bis(4-substituted-4-aminobutyl)amines. Tetrahedon Asymmetry 16, 739-743 (2005).
  5. N. Kinoshita, K. H. Marx, K. Tanaka, K. Tsubaki, T. Kawabata, N. Yoshikai, E. Nakamura, K. Fuji, Enantioselective Allylic Substitution of Cinnamyl Esters Catalyzed by Iridium-Chiral Aryl Phosphite Complex: Conspicuous Change in the Mechanistic Spectrum by a Countercation and Solvent J. Org. Chem. 69, 7960-7964 (2004).
  6. K. Tsubaki, M. Miura, H. Morikawa, H. Tanaka, T. Kawabata, T. Furuta, K. Tanaka, K. Fuji, Synthesis of Optically Active Oligonaphthalenes via Second-Order Asymmetric Transformation J. Am. Chem. Soc. 125, 16200-16201 (2003)
  7. T. Kawabata, S. Kawakami, S. Majumdar, Asymmetric Cyclization via Memory of Chirality: A Concise Access to Cyclic Amino Acids with a Quaternary Stereocenter J. Am. Chem. Soc. 125, 13012-13013 (2003)
  8. T. Kawabata, Asymmetric Construction of Quaternary Carbon Centers. Farumashia 39, 114-115 (2003)
  9. T. Kawabata, O. Ozturk, H. Suzuki, K. Fuji, A Facle Asymmetric Stythesis of Tetrahydroisoquioline and Tryptoline Derivatives with a Quaternary Carbon Center at C(3). Synthesis 505-508 (2003)
  10. T. Kawabata, K Fuji, Memory of Chirality: Asymmetric Induction Based on Dynamic Chirality of Enolates. Topics in Stereochemistry; S. E. Denmark Ed., John Wiley & Sons, New York 23, 175-205 (2003)
  11. T. Kawabata, R. Stragies, T. Fukaya, Y. Nagaoka, H. Schedel, K. Fuji, Preparation and Properties of Chiral 4-Pyrrolidinopyridine (PPY) Analogues with Dual Functional Side Chains. Tetrahedon Lett. 44, 1545-1548 (2003)
  12. T. Kawabata, S. Kawakami, S. Shimada, K. Fuji, Control of the Enantioselectivity of Alkylation of Phenylalanine Derivatives by Regulation of the Aggregate Structure of Chiral Enolate Intermediates. Tetrahedron 59, 965-974 (2003)
  13. T. Kawabata, O. Ozturk, J. Chen, K. Fuji, Chirality Transfer during Alkylation of Chiral Amides. Chem. Comm. 162-163 (2003)
  14. T. Kawabata, R. Stragies, T. Fukaya, K. Fuji, Remote Chirality Transfer in Nucleophilic Catalysis with N-(4-Pyridinyl)-L-Proline Derivatives. Chirality 15, 71-76 (2003)
  15. T. Kawabata, K. Fuji, Memory of Chirality: Asymmetric C-C Bond Formation via Enolate Intermediates with Dynamic Chirality. J. Syn. Org. Chem. Jpn 58, 66-67 (2002)
  16. T. Kawabata, S. Kawakami, K. Fuji, Enantioselective α-Allylation of a Phenylalanine Derivative under the Control of Aggregation of a Chiral Nonracemic Enolate. Tetrahedron Lett. 43, 1465-1467 (2002)
  17. T. D. Bagul, G. Lakshmaiah, T. Kawabata, K. Fuji, Total Synthesis of Sporotryprostatin B via Asymmetric Nitroolefination. Org. Lett. 4, 249-251 (2002)
  18. T. Kawabata, Nucleophilic Catalysis: Asymmetric Synthesis, Substrate-Specific Reactions and Multi-Component Sequential Reactions. J. Syn.Org. Chem. Jpn 59, 458-459 (2001)
  19. T. Kawabata, Discrimination of Enantiomers by an Artificial Enzyme. Advanced Enzyme-based Techniques with Comprehensive Applications; M. Aizawa : Ed. CMC, Tokyo 71-81 (2001)
  20. T. Kawabata, Discrimination of Enantiomers by an Artificial Enzyme. Bio Industry 18, 17-24 (2001)
  21. T. Kawabata, K. Yamamoto, Y. Momose, H. Yoshida, Y. Nagaoka, K. Fuji, Kinetic Resolution of Amino Alcohol Derivatives with a Chiral Nucleophilic Catalyst: Access to Enanatiopure cis-Cyclic Amino Alcohols. Chem. Comm. 2700-2701 (2001)
  22. T. Kawabata, K Fuji, Memory of Chirality: Alkylation of α-Amino Acid Derivatives. J. Syn. Org. Chem. Jpn. 58, 1095-1099 (2000)
  23. T. Kawabata, Asymmetric Synthesis Based on Enolate Chemistry: β-Lactam Synthesis and Memory of Chirality. Reviews on Heteroatom Chemistry 22, 33-58 (2000)
  24. T. Kawabata, J. Chen, H. Suzuki, Y. Nagae, T. Kinoshita, S. Chacharunee, K. Fuji, Memory of Chirality in Diastereoselective α-Alkylation of Isoleucine and allo-Isoleucine Derivatives. Org. Lett 2, 3883-3885 (2000)
  25. T. Kawabata, H. Suzuki, Y. Nagae, K. Fuji, A Chiral Nonracemic Enolate with Dynamic Axial Chirality: Direct Asymmetric α-Methylation of α-Amino Acid Derivatives. Angew. Chem. Int. Ed. 39, 2155-2157 (2000)
  26. K. Fuji, H. Ohnishi, S. Moriyama, K. Tanaka, T. Kawabata, K. Tsubaki, Palladium-Catalyzed Asymmetric Allylic Alkylation with a Chiral Monodentate Phophine Ligand: 8-Diphenylphosphino-8'-methoxy-1,1'-binaphthyl. Synlett 351-352 (2000)
  27. K. Fuji, N. Kinoshita, K. Tanaka, T. Kawabata, Enantioselective Allylic Substituion Catalyzed by an Iridium Complex: Remarkable Effects of the Counter Cation Chem. Comm 2289-2290 (1999)
  28. J. Chen, T. Kawabata, H. Ohnishi, M. Shang, K. Fuji, Lewis Acid-Promated Nitroolefination of Enol Silyl Ethers via an Addition Elimanation Process. Chem. Pharm. Bull 47, 394-397 (1999)
  29. G. Lakshmaiah, T. Kawabata, M. Shang, K. Fuji, Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination. J. Org. Chem. 64, 1699-1704 (1999)
  30. K. Fuji, T. Kawabata, Memory of Chirality: A New Principle in Enolate Chemistry. Chem. Eur. J. 4, 373-376 (1998)
  31. Kawabata T, Fuji K, Carbon-Carbon Bond Formation Asymmetric Synthesis, Kodansha, Tokyo 184, 216, 285, 337
  32. K. Fuji, M. Sakurai, T. Kinoshita, T. Kawabata, Palladium-Catalyzed Asymmetric Reduction of Allylic Esters with a New Chiral monodentate Lgand, 8-Diphenylphosphino-8'-Methoxy-1,1'-binaphthyl. Tetrahedron Lett. 39, 6323-6326 (1998)
  33. K. Fuji, T. Oka, T. Kawabata, T. Kinoshita, The First Synthesis of an Optically Active Molecular Bevel Gear with Only Two Cogs on Each Wheel. Tetrahedron Lett. 39, 1373-1376 (1998)
  34. K. Fuji, T. Kawabata, T. Ohmori, M. Shang, M. Node, Enantioselective Creation of Quartenary Carbon Centers through Addition-Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles. Heterocycles 47, 951-964 (1998)
  35. K. Fuji, M. Sakurai, T. Kinoshita, T. Tada, A. Kuroda, T. Kawabata, Assessment of the Activity of 8-Diphenylphosphino-8'-methoxy-1,1'-binaphthyl as a Ligand for Palladium-Catalyzed Reactions. Chem. Pharm. Bull. 45, 1524-1526 (1997)
  36. T. Kawabata, M. Nagato, K. Takasu, K. Fuji, Nonenzymatic Kinetic Resolution of Racemic Alcohols through an "Induced Fit" Process. J. Am. Chem. Soc. 119, 3169-3170 (1997)
  37. K. Fuji, M. Sakurai, N. Tohkai, A. Kuroda, T. Kawabata, Y. Fukazawa, T. Kinoshita, T. Tada, Unexpectedly Facile Racemization of 8-Diphenylphosphinoyl-8'-methoxy-1,1'-binaphthyl. J. C. S. Chem. Comm 1609-1610 (1996)
  38. T. Kawabata, A. Kuroda, E. Nakata, K. Fuji, Chiral Recognition of Amino Acid Derivatives by 1,1'-Binaphthalene-8,8'-diol. Tetrahedron Lett. 37, 4153-4156 (1996)
  39. K. Fuji, T. Kawabata, Y. Kiryu, Y. Sugiura, Ring Opening of Optically Active cis-Disubstituted Aziridino Alcohols: An Enantiodivergent Synthesis of Functionalized Amino Alcohol Derivatives. Heterocycles 701-715 (1996)
  40. T. Kawabata, Memory of Chirality: An Idea Realizing Unusual Organic Reactions. Chemistry Today 287, 16-21 (1995)
  41. T. Kawabata, Asymmetric Synthesis Based on Enolate Chemistry: β-Lactam Synthesis and Memory of Chirality. Journal of the Pharmaceutical Society of Japan 115, 700-722 (1995)
  42. T. Kawabata, K. Fuji, Memory of Chirality: A New Concept for Enolate Chemistry. Cemistry and Chemical Industry (Japan) 48, 1039-1042 (1995)
  43. K. Fuji, T. Kawabata, T. Ohmori, M. Node, An Enantioselective Synthesis of (-)-Pseudophrynaminol through Asymmetric Nitroolefination. Synlett 367-368 (1995)
  44. K. Fuji, T. Kawabata, A. Kuroda, Enantioselective Protonation of Enolates: Novel Chiral Proton Sources and Remarkable Effects of the Counter Cation. J. Org. Chem. 60, 1914-1915 (1995)
  45. T. Kawabata, K. Fuji, J. Syn, Memory of Chirality. J. Syn. Org. Chem. Jpn. 52, 589-595 (1994)
  46. T. Kawabata, T. Wirth, K. Yahiro, H. Suzuki, K. Fuji, Direct Asymmetric α-Alkylation of Phenylalanine Derivatives Using No External Chiral Sources. J. Am. Chem. Soc. 116, 10809-10810 (1994)
  47. K. Fuji, T. Kawabata, Y. Naniwa, T. Ohmori, M. Node, Enhanced Reactivity of Zinc Enolates over Lithium Enolates in Asymmetric Nitroolefination. Chem. Pharm. Bull. 42, 999-1001 (1994)
  48. T. Kawabata, K. Fuji, Asymmetric Carbon-Carbon Bond Formation. Chemistry and Biology 31, 817-825 (1993)
  49. T. Kawabata, Y. Kiryu, Y. Sugiura, K. Fuji, An Enantiodivergent Synthesis of threo &beta-Amino Alcohols: Preparation of Key Intermediates for Bestatin and the Related Peptides. Tetrahedron Lett. 34, 5127-5130 (1993)
  50. M. Node, A. Itoh, K. Nishide, H. Abe, T. Kawabata, Y. Masaki, K. Fuji, Preparation of Nitroalkenes: Substitution Reaction via Addition-Elimination Using β-Nitrovinyl Sulfoxides. Synthesis 1119-1124 (1992)
  51. K. Fuji, T. Kawabata, M. Ueda, M. Fujimoto, E. Fujita, M. Node, Hard Acid and Soft Nucleophile Systems. Part 14. On the Reactivity of α-Nitroketones and Nitroolefins Toward an Aluminum Chloride and Ethanethiol System. Bulletin of the Institute for Chemical Research, Kyoto University 70, 318-325 (1992)
  52. T. Kawabata, T. Minami, T. Hiyama, Stereoselective Synthesis of β-Lactams by Oxidaitive Coupling of Dianions of Acyclic Tertiary Amides. J. Org. Chem 57, 1864-1873. (1992)
  53. T. Kawabata, K. Yahiro, K. Fuji, Memory of Chirality: Enantioselective Alkylation Reactions at an Asymmetric Carbon Adjacent to a Carbonyl Group. J. Am. Chem. Soc. 113, 9694-9696 (1991)
  54. K. Fuji, S. P. Khanapure, M. Node, T. Kawabata, A. Itoh, Y. Masaki, Hard Acid and Soft Nucleophile Systems. Part 12. Regioselective Functionalization of 1,3-Dienes through the Lewis Acid Mediated Thienium Cation Diels-Alder Reaction. Tetrahedron 46, 7393-7402 (1990)
  55. K. Fuji, T. Kawabata, Y. Kiryu, Y. Sugiura, T. Taga, Y. Miwa, A New Access to Chiral Aziridines by Enzymatic Transesterification of meso-Bis- (acetoxymethyl)aziridines. Tetrahedron Lett 31, 6663-6666 (1990)
  56. K. Fuji, M. Node, Y. Naniwa, T. Kawabata, Enantioselective Iodolactonization through Diastereotopic Group Differentiation. Tetrahedron Lett. 31, 3175-3178 (1990)
  57. Y, Itoh, Y, Kobayashi, T. Kawabata, M, Takase, S. Terashima, Novel Synthesis of the Carbapenem Key Intermediates, (3R, 4R)-4-Acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S, 4R)-3-[(R)-1-(t-Butyldimethylsilyl-oxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-Ethyl Lactate. Tetrahedron 45, 5767-5790 (1989)
  58. T. Kawabata, K. Itoh, T. Hiyama, Regio- and Chemoselective Epimerization of cis-3-Amino-β-Lactams to the trans-Isomers: A New Synthesis of Aztreonam. Tetrahedron Lett. 4837-4840
  59. T. Kawabata, K. Sumi, T. Hiyama, A New Synthesis of β-Lactams through Stereoselective Oxidative Coupling of the Dianions of Acyclic Amides. J. Am.¡¡Chem. Soc 111, 6843-6845 (1989)
  60. N. Takahashi, H. Osada, N. Numao, H. Saimoto, T. Kawabata, T. Hiyama, Differentiation Induction of Human Promyelocytic Leukemia Cells with Colletochlorin B and its Analogues. Chem. Pharm. Bull 36, 452-455 (1988)
  61. T. Kawabata, Y. Kimura, Y. Ito, S. Terashima, A. Sasaki, M. Sunagawa, A Novel and Efficient Synthesis of the Key Intermediate of 1β-Methylcarbapenem Antibiotics Employing [2+2]-Cycloaddition Reaction of Diketene with a Chiral Imine. Tetrahedron 44, 2149-2165 (1988)
  62. K. Fuji, M. Node, T. Kawabata, M. Fujimoto, Hard Acid and Soft Nucleophile Systems. Part 11. Hard-Soft Affinity Inversion: Dehalogenation of a-Halogeno Ketones with Aluminum Chloride and a Thiol. J.C. S. Perkin I 1043-1047 (1987)
  63. T. Kawabata, P.A. Grieco, H-L. Sham, H. Kim, J.Y. Jaw, S. Tu, Model Studies in the Quassimarin Series: Total Synthesis of De-A-quassimarin. J. Org. Chem 52, 3346-3354 (1987)
  64. T. Kawabata, Y. Kimura, Y. Ito, S. Terashima, A. Sasaki, M. Sunagawa, A Novel and Efficient Synthesis of the Key Intermediate of 1b-Methylcarbapenem Antibiotics from (S)-Methyl 3-hydroxy-2-methylpropionate. Tetrahedron Lett. 27, 6241-6244 (1986)
  65. Y. Ito, T. Kawabata, S. Terashima, A Novel Synthesis of (3R,4R)-4-Acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone, the Versatile Key Intermediate of Carbapenem Synthesis, from (S)-Ethyl Lactate. Tetrahedron Lett. 27, 5751-5754 (1986)
  66. M. Node, T. Kawabata, E. Fujita, K. Fuji, Hard Acid and Soft Nucleophile Systems 10. The Mechanistic Study for Debromination of para-Bromoanisole with Aluminum Chloride and Ehtanethiol. Bulletin of the Institute for Chemical Research, Kyoto University 63, 47-51
  67. K. Fuji, S.P. Khanapure, M. Node T. Kawabata, A. Ito, Lewis Acid Mediated Thienium Cation Diels -Alder Reaction: A New Method for Regio- and Stereoselective Functionalization of 1,3-Dienes. Tetrahedron Lett. 26, 779-782 (1985)
  68. K. Fuji, M. Node, T. Kawabata, M. Fujimoto, Hard-Soft Affinity Inversion: Dehalogenation of &alpha-Haloketones. Chem. Lett. 1153-1156 (1984)
  69. M. Node, T. Kawabata, K. Ohta, M. Fujimoto, E. Fujita, K. Fuji, Hard Acid and Soft Nucleophile Systems 8. Reductive Dehalogenation of o- and p-Halophenols and Their Derivatives. J. Org. Chem 49, 3641-3643 (1984)
  70. K. Fuji, T. Kawabata, M. Node, E. Fujita, Hard Acid and Soft Nucleophile Systems 9. Cleavage of Activated Carbon-Carbon Double Bonds with a Hard Lewis Acid and Ethanethiol. J. Org. Chem 49, 3214-3216 (1984)
  71. M. Node, T. Kawabata, M. Fujimoto, K. Fuji, General Synthesis of 1-Ethylthio-2-nitroolefins. Synthesis 234-236 (1984)
  72. M. Node, K. Nishide, T. Kawabata, K. Ohta, K. Watanabe, K. Fuji, E. Fujita, Hard Acid and Soft Nucleophile System. VII. A Convenient Reduction of Functionalized Polyarenes into Parent Polyarenes. Chem. Pharm. Bull. 31, 4306-4311 (1983)
  73. M. Node, T. Kawabata, K. Ohta, K. Watanabe, K. Fuji, E. Fujita, Radical Cation Induced Reductive Dehalogenation of ortho- and para-Halophenols and Their Derivatives. Chem. Pharm. Bull. 31, 749-751 (1983)
  74. M. Node, T. Kawabata, M. Ueda, M. Fujimoto, K. Fuji, E. Fujita, Reductive Displacement of the Nitro Group into Hydrogen in Primary α-Nitroketones. Tetrahedron Lett. 23, 4047-4050 (1982)
  75. K. Fuji, T. Kawabata, M. Node, E. Fujita, Carbon-Carbon Double Bond Cleavage with a Hard Lewis Acid and Ethanethiol. Tetrahedron Lett. 22, 875-878 (1981)
  76. K. Fuji, T. Kawabata, E. Fujita, Hard Acid and Soft Nucleophile System. IV. Removal of Benzyl Protecting Group with Boron Trifluoride Etherate and Dimethyl Sulfid. Chem. Pharm. Bull. 28, 3662-3664 (1980)

Update: November 16, 2005