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戦略的基礎研究推進事業 平成7年度採択研究課題 研究終了報告  469-487
高次構造を有する有機分子の極微細触媒構造を機軸とする立体選択的構築
福山 透


主な研究成果
(1)論文発表 (国内6件、海外138件)
T. Fukuyama and G. Liu
Stereocontrolled Total Synthesis of (±)-Gelsemine.
J. Am. Chem. Soc, 118, 7426 (1996)
T. Fukuyama and G. Liu
Stereocontrolled Total Synthesis of (±)-Gelsemine
Pure Appl. Chem., 69, 501 (1997)
T. Fukuyama, M. Cheung, C.-K. Jow, Y. Hidai, and T. Kan
2,4-Dinitrobenzenesulfonamides: A Simple and Practical Method for the Preparation of Secondary Amines and Diamines
Tetrahedron Lett., 38, 5831-5834 (1997)
E. Arai, H. Tokuyama, M. S. Linsell, and T. Fukuyama
2-(2-Aminophenyl)-acetaldehyde Dimethyl Acetal: A Novel Reagent for the Protection of Carboxylic Acid
Tetrahedron Lett., 39, 71-74 (1998)
H. Tokuyama, S. Yokoshima, T. Yamashita, and T. Fukuyama
A Novel Ketone Synthesis by a Palladium-Catalyzed Reaction of Thiol Esters and Organozinc Reagents
Tetrahedron Lett., 39, 3189-3192 (1998)
N. Waizumi, T. Itoh, and T. Fukuyama
Synthetic Studies on CP-225,917 and CP-263,114
Tetrahedron Lett., 39, 6015-6018 (1998)
Y. Kobayashi and T. Fukuyama
Development of a Novel Indole Synthesis and Its Application to Natural Products Synthesis
J. Heterocyclic Chem. 35, 1043 (1998)
H. Tokuyama, S. Yokoshima, T. Yamashita, S.-C. Lin, L. Li, and T. Fukuyama
Facile Palladium-Mediated Conversion of Ethanethiol Esters to Aldehydes and Ketones
J. Braz. Chem. Soc., 9, 381-387 (1998)
H. Tokuyama, T. Yamashita, M. T. Reding, Y. Kaburagi, and T. Fukuyama
Radical Cyclization of 2-Alkenylthioanilides: A Novel Synthesis of 2,3-Disubstituted Indoles
J. Am. Chem. Soc., 121, 3791-3793 (1999)
Y. Kobayashi, T. Fujimoto, and T. Fukuyama
Stereocontrolled Total Synthesis of (+)-K252a.
J. Am. Chem. Soc., 121, 6501-6502 (1999)
M.T. Reding and T. Fukuyama
Stereocontrolled Total Synthesis of (±)-Catharanthine via Radical-Mediated Indole Formation
Org. Lett., 1, 973-976 (1999)
A. Endoh, T. Kan, and T. Fukuyama
Synthetic Study on Ecteinascidin 743 Starting from D-Glucose
Synlett, 1103-1105 (1999)
T. Fukuyama, M. Cheung, and T. Kan
N-Carboalkoxy-2-Nitrobenzenesulfonamides: A Practical Preparation of N-Boc-, N-Alloc-, and N-Cbz-Protected Primary Amines
Synlett, 1301-1303 (1999)
S. Kobayashi, G. Peng, and T. Fukuyama.
Efficient Total Synthesis of (±)-Vincadifformine and (-)-Tabersonine.
Tetrahedron Lett., 40, 1519-1522 (1999)
Y. Hidai, T. Kan, and T. Fukuyama
Total Synthesis of Polyamine Toxin HO-416b Utilizing the 2-Nitrobenzenesulfonamide Protecting Group
Tetrahedron Lett., 40, 4711-4714 (1999)
N. Waizumi, T. Itoh, and T. Fukuyama
Total Synthesis of (-)-CP-263,114 (Phomoidride B)
J. Am. Chem. Soc., 122, 7825-7826 (2000)
S. Yokoshima, H. Tokuyama, and T. Fukuyama
Enantioselective Total Synthesis of (+)-Gelsemine: Determination of Its Absolute Configuration
Angew. Chem. Int. Ed., 39, 4073-4075 (2000)
S. Kobayashi, T. Ueda, and T. Fukuyama
An Efficient Total Synthesis of Vindoline
Synlett, 883-886 (2000)
A. Fujiwara, T. Kan, and T. Fukuyama
Total Synthesis of Lipogrammistin-A
Synlett, 1667-1669 (2000)
Y. Hidai, T. Kan, and T. Fukuyama
Total Synthesis of Polyamine Toxin HO-416b and Agel-489 Using a 2-Nitrobenzenesulfonamide Strategy
Chem. Pharm. Bull., 48, 1570-1576 (2000)
H. Tokuyama, Y. Kaburagi, X. Chen, and T. Fukuyama,
Synthesis of 2,3-Disubstituted Indoles by Palladium-Mediated Coupling of 2-Iodoindes
Synthesis, 429-434 (2000)
H. Tokuyama, T. Kuboyama, A. Amano, T. Yamashita, and T. Fukuyama
A Novel Transformation of Primary Amines to N-Monoalkylhydroxylamines
Synthesis, 1299-1304 (2000)
H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama
A Practical Synthesis Quinoline form Anilines
Heterocycles, 54, 105-108 (2001)
S. Tohma, A. Endo, T. Kan, and T. Fukuyama
Synthesis of Optically Active Arylglycines: Stereoselective Mannich Reaction of Phenols with a New Chiral Template
Synlett, in press.
T. Kan and T. Fukuyama
Highly Versatile Synthesis of Nitrogen-Containing Compounds by Means of Nitrobenzenesulfonamides
J. Syn. Org. Chem. Jpn, in press.
H. Tokuyama, T. Makido, T. Ueda, and T. Fukuyama
One-Pot Claisen Rearrangement with n-Butyl Vinyl Ether
Syn. Commun., in press.
T. Arai, H. Sasai, K.-I. Aoe, K. Okamura, T. Date, and M. Shibasaki
A New Hetero-Bimetallic Multifunctional Asymmetric Catalyst (Al-Li-BINOL Complex) for Michael Reactions and Tandem Michael-Aldol Reactions
Angew. Chem. Int. Ed., 35, 104-106 (1996)
T. Arai, M. Bougauchi, H. Sasai, and M. Shibasaki
Catalytic Asymmetric Synthesis of a-Hydroxy Phosphonates Using the Al-Li-BINOL Complex (ALB)
J. Org. Chem., 61, 2926-2927 (1996)
H. Sasai, E. Emori, T. Arai, and M. Shibasaki
Catalytic Asymmetric Michael Reactions Promoted by the La-Na-BINOL Complex (LSB). Enantioface Selection on Michael Donors
Tetrahedron Lett., 37, 5561-5564 (1996)
T. Arai, Y.M.A. Yamada, N. Yamamoto, H. Sasai, and M. Shibasaki
Self-Assembly of Heterobimetallic Complexes and Reactive Nucleophiles: A General Strategy for the Activation of Asymmetric Reactions Promoted by Heterobimetallic Catalysts
Chem. Eur. J., 2, 1368-1372 (1996)
K. Iseki, S. Oishi, H. Sasai, and M. Shibasaki
Catalytic Asymmetric Nitroaldol Reaction of α,α-Difluoro Aldehydes Mediated by Rare Earth-Lithium-BINOL Complexes
Tetrahedron Lett., 37, 9081-9084 (1996)
H. Groger, J. Martens, H. Sasai, Y. Saida, and M. Shibasaki
First Catalytic Asymmetric Hydrophosphonylation of Cyclic Imines: Highly Efficient Enantioselective Approach to a 4-Thiazolidinyl-Phosphonate via Chiral Titanium and Lanthanoid Catalysts
Tetrahedron Lett., 37, 9291-9292 (1996)
H. Sasai, S. Watanabe, and M. Shibasaki
A New Practical Preparation Method for Lanthanum-Lithium-Binaphthol Catalysts (LLBs) for Use in Asymmetric Nitroaldol Reactions
Enantiomer, 2, 267-271 (1997)
M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, and M. Shibasaki
Catalytic Asymmetric Epoxidation of α,α-Unsaturated Ketones Promoted by Lanthanoid Complexes
J. Am. Chem. Soc., 119, 2329-2330 (1997)
H. Sasai, M. Bougauchi, T. Arai, and M. Shibasaki
Enantioselective Synthesis of α-Hydroxy Phosphonates Using the LaLi3tris(binaphthoxide) Catalyst (LLB), Prepared by an Improved Method
Tetrahedron Lett., 38, 2717-2720 (1997)
T. Iida, N. Yamamoto, H. Sasai, and M. Shibasaki
The New Asymmetric Reactions Using Gallium Complex: Highly Enantioselective Ring Opening of Epoxides Catalyzed by GaLibis(binaphthoxide) Complex (GaLB)
J. Am. Chem. Soc., 119, 4783-4784 (1997)
Y.M.A. Yamada, N. Yoshikawa, H. Sasai, and M. Shibasaki
Direct Catalytic Asymmetric Aldol Reactions of Aldehydes with Unmodified Ketones
Angew. Chem. Int. Ed., 36, 1871-1873 (1997)
E. Takaoka, N. Yoshikawa, Y.M.A. Yamada, H. Sasai, and M. Shibasaki
Catalytic Asymmetric Synthesis of Arbutamine
Heterocycles, 46, 157-163 (1997)
H. Sasai, M. Hiroi, Y.M.A. Yamada, and M. Shibasaki
The First Tandem Inter-intramolecular Catalytic Asymmetric Nitroaldol Reaction Utilizing a LnLi3tris((R)-binaphthoxide) Complex ((R)-LnLB) (Ln: Lanthanoid)
Tetrahedron Lett., 38, 6031-6034 (1997)
M. Sodeoka, R. Tokunoh, F. Miyazaki, E. Hagiwara, and M. Shibasaki
Stable Diaqua Palladium(II) Complexes of BINAP and Tol-BINAP as Highly Efficient Catalysts for Aymmetric Aldol Reactions
Synlett, 463-466 (1997)
M. Shibasaki, H. Sasai, and T. Arai
Catalytic Asymmetric Carbon-Carbon Bond-Forming Reaction Utilizing Rare Earth Metal Complexes
Med. Chem.: Today and Tomorrow, 105-112 (1997)
M. Shibasaki, C.D.J. Boden, and A. Kojima
The Asymmetric Heck Reaction
Tetrahedron, 53, 7371-7395 (1997)
K. Iseki, S. Oishi, H. Sasai, and M. Shibasaki
Synthesis and Biological Evaluation of a Fluorinated Analog of the β-Adrenergic Blocking Agent, Metoprolol
Bioorg. Med. Chem. Lett., 7, 1273-1274 (1997)
R. Gotlich, K. Yamakoshi, H. Sasai, and M. Shibasaki
A New and Selective Metal-Catalyzed Baeyer-Villiger Oxidation Procedure.
Synlett, 8, 971-973 (1997)
A. Kojima, Shinobu Honzawa, Christopher D.J. Boden, and M. Shibasaki
Tandem Suzuki Cross-coupling-Heck Reactions
Tetrahedron Lett., 38, 3455-3458 (1997)
A. Kojima, C.D.J. Boden, and M. Shibasaki
Synthesis and Evaluation of a New Chiral Arsine Ligand; 2,2′-bis(diphenylarsino)- 1,1′-binaphthyl (BINAs)
Tetrahedron Lett., 38, 3459-3460 (1997)
M. Shibasaki, H. Sasai, and T. Arai
Asymmetric Catalysis with Heterobimetallic Compounds
Angew. Chem. Int. Ed., 36, 1236-1356 (1997)
S.Y. Cho, and M. Shibasaki
Synthesis and Evaluation of A New Chiral Ligand: 2-Diphenylarsini-2′-diphenylphosphino-1,1′-binaphthyl (BINAPAs)
Tetrahedron Lett., 39, 1773-1776 (1998)
M. Sodeoka, M.A. Arai, K. Adachi, K. Uotsu, and M. Shibasaki.
Rational Design, Synthesis, and Evaluation of a New Type of PKC Inhibitor
J. Am. Chem. Soc., 120, 457-458 (1998)
T. Arai, H. Sasai, K. Yamaguchi, and M. Shibasaki
Regioselective Catalytic Asymmetric Reaction of Horner-Wadsworth-Emmons Reagents with Enones: The Odyssey of Chiral Aluminum Catalysts
J. Am. Chem. Soc., 120, 441-442 (1998)
H. Groer, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, and M. Shibasaki
A New and Highly Efficient Asymmetric Route to Cyclic α-Amino Phosphonates: The First Catalytic Enantioselective Hydrophosphonylation of Cyclic Imines Catalyzed by Chiral Heterobimetallic Lanthanoid Complexes
J. Am. Chem. Soc., 120, 3089-3103 (1998)
E. Emori, T. Arai, H. Sasai, and M. Shibasaki.
A Catalytic Michael Addition of Thiols to a,b-Unsaturated Carbonyl Compounds: Asymmetric Michael Additions and Asymmetric Protonations
J. Am. Chem. Soc., 120, 4043-4044 (1998)
柴崎正勝, 飯田剛彦, 山田陽一
多点制御型不斉触媒の創製と実践的有機合成への展開
有機合成化学協会誌, 56, 344-356 (1998)
T. Morita, T. Arai, H. Sasai, and M. Shibasaki
Utilization of Heterobimetallic Complexes as Lewis Acids
Tetrahedron: Asymmetry, 9, 1445-1450 (1998)
M. Sodeoka and M. Shibasaki
Asymmetric Synthesis Using Palladium Catalysts
Pure Appl. Chem., 70, 411-414 (1998)
K. Yamada, T. Arai, H. Sasai, and M. Shibasaki
A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex
J. Org. Chem., 63, 3666-3672 (1998)
Y.M.A. Yamada and M. Shibasaki
Direct Catalytic Asymmetric Aldol Reactions Promoted by a Novel Barium Complex
Tetrahedron Lett., 39, 5561-5564 (1998)
M. Shibasaki, H. Sasai, T. Arai, and T. Iida.
Heterobimetallic Asymmetric Catalysts. Developments and Applications
Pure Appl. Chem., 70, 1027-1034 (1998)
M. Shibasaki and K. Uotsu
PKC Activations and Inhibitors
IGAKUSHOIN, 49, 290-295 (1998)
K. Uotsu, M. Sodeoka, and M. Shibasaki
Photoaffinity Labeling of PKC Isozymes by Phorbol Ester Derivatives
Bioorg. Med. Chem., 6, 1117-1126 (1998)
New Catalytic Concepts for the Asymmetric Aldol Reaction
H. Gröger, E.M. Vogl, and M. Shibasaki
Chem. Eur. J., 4, 1137-1141 (1998)
T. Iida, N. Yamamoto, H.-G. Woo, and M. Shibasaki
Enantioselective Ring Opening of Epoxides with 4-Methoxyphenol Catalyzed byGallium Heterobimetallic Complexes: An Efficient Method for the Synthesis of Optically Active 1,2-Diol Monoethers
Angew. Chem. Int. Ed., 37, 2223-2226 (1998)
E.M. Vogl, S. Matsunaga, M. Kanai, T. Iida, and M. Shibasaki
Linking BINOL: C2-Symmetric Ligands for Investigations on Asymmetric Catalysis
Tetrahedron Lett., 39, 7917-7920 (1998)
F. Miyazaki, K. Uotsu, and M. Shibasaki
Silver Salt Effects on an Asymmetric Heck Reaction Catalytic Asymmetric Total Synthesis of (+)-Xestoquinone
Tetrahedron, 54, 13073-13078 (1998)
S. Shimizu, K. Ohori, T. Arai, H. Sasai, and M. Shibasaki
A Catalytic Asymmetric Synthesis of Tubifolidine
J. Org. Chem., 63, 7547-7551 (1998)
K. Funabashi, Y. Saida, M. Kanai, T. Arai, H. Sasai, and M. Shibasaki
Catalytic Asymmetric Michael Adition of Nitromethane to Enones Controlled by (R)-LPB
Tetrahedron Lett., 39, 7557-7558 (1998)
S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi, and M. Shibasaki
Water vs. Desiccant. Improvement of Yb-BINOL Complex Catalyzed Enantioselective Epoxidation of Enones
Tetrahedron Lett., 39, 7353-7356 (1998)
M. Shibasaki, A. Kojima, and S. Shimizu
Catalytic Asymmetric Synthesis of Natural Products with Heterocyclic Rings
J. Heterocyclic Chem, 35, 1057-1064 (1998)
S. Watanabe, T. Arai, H. Sasai, M. Bougauchi, and M. Shibasaki
The First Catalytic Enatioselective Synthesis of cis-Epoxyketones from cis-Enones
J. Org. Chem., 63, 8090-8091 (1998)
S.Y. Cho and M. Shibasaki
The Symmetric Synthesis of Cyclopentane Derivatives by Palladium-catalyzed Coupling of Prochiral Alkylboron Compounds
Tetrahedron: Asymmetry, 9, 3751-3754 (1998)
S. Yamasaki, T. Iida, and M. Shibasaki
Direct Catalytic Asymmetric Mannich-type Reaction of Unmodified Ketones Utilizing the Cooperation of an AlLibis(binaphthoxide) Complex and La(OTf)3·H2O
Tetrahedron Lett., 40, 307-310 (1999)
S. Honzawa, T. Mizutani, and M. Shibasak
Synthetic Studies on (+)-Wortmannin. An Asymmetric Construction of an Allylic Quaternary Carbon Center by a Heck Reaction
Tetrahedron Lett., 40, 311-314 (1999)
K. Yamakoshi, S. Harwood, M. Kanai, and M. Shibasaki
Catalytic Asymmetric Addition of Diphenylphosphine Oxide to Cyclic Imines
Tetrahedron Lett., 40, 2565-2568 (1999)
Y. Hamashima, D. Sawada, M. Kanai, and M. Shibasaki
A New Bifunctional Asymmetric Catalysis: An Efficient Catalyitc Asymmetric Cyanosilylation of Aldehydes
J. Am. Chem. Soc., 121, 2641-2642 (1999)
N. Yoshikawa, Y.M.A. Yamada, J. Das, H. Sasai, and M. Shibasaki
Direct Catalytic Asymmetric Aldol Reaction
J. Am. Chem. Soc., 121, 4168-4178 (1999)
H. Sato, Y.S. Kim, and M. Shibasaki
A Catalytic Asymmetric Synthesis of a Versatile Intermediate for Phorbol Derivatives
Tetrahedron Lett., 40, 2973-2976 (1999).
M. Shibasaki and E.M. Vogl
The Palladium-Catalysed Arylation and Vinylation of Alkenes-Enantioselective Fashion
J. Organomet. Chem., 576, 1-15 (1999).
M. Kanai, Y. Hamashima, and M. Shibasaki
Design and Development of Lewis acid-Lewis base Bifunctional Asymmetric Catalyst
Pharmacia, 35, 690-694 (1999).
E. Emori, T. Iida, and M. Shibasaki
Catalytic Kinetic Resolution Reaction of (±)-5-Methylbicyclo[3.3.0]-oct-1-ene-3,6-dione
J. Org. Chem., 64, 5318-5320 (1999)
S. Yamasaki, T. Iida, and M. Shibasaki
Direct Catalytic Asymmetric Mannich Reaction of Unmodified Ketons: Cooperative Catalysis of an AlLibis(binaphthoxide) Complex and La(OTf)3
Tetrahedron, 55, 8857-8867 (1999)
E.M. Vogl, H. Groeger, and M. Shibasaki
Towards Perfect Asymmetric Catalysis: Additives and Cocatalysts
Angew. Chem. Int. Ed., 38, 1570-1577 (1999)
F. Miyazaki, K. Yamaguchi, and M. Shibasaki
The Synthesis of a New Palladacycle Catalyst. Development of a High Performance Catalyst for Heck Reactions
Tetrahedron Lett., 40, 7378-7383 (1999)
K. Yamada, S. J. Harwood, H. Groeger, and M. Shibasaki
The First Catalytic Asymmetric Nitro-Mannich-Type Reaction Promoted by a New Heterobimetallic Complex.
Angew. Chem. Int. Ed., 38, 3504-3506 (1999)
M. Shibasaki
Multifunctional Asymmetric Catalysis
CHEMTRACTS-ORGANIC CHEMISTRY, 12, 978-988 (1999).
M. Shibasaki
Phorbols: Chemical Synthesis and Chemical Biology
YAKUGAKU ZASSHI, 120, 76-90 (2000)
A. Sekine, N. Kumagai, K. Uotsu, T. Ohshima, and M. Shibasaki
An Efficient Method for the Synthesis of Versatile Intermediates Leading to 13-Deoxy- and 9,13-Dideoxyphorbols.
Tetrahedron Lett., 41, 509-513 (2000)
I. Sakurada, S. Yamasaki, R. Goetlich, T. Iida, M. Kanai, and M. Shibasaki
Direct Chlorohydrin and Acetoxy Alcohol Synthesis from Olefins Promoted by a Lewis Acid, Bis(trimethylsilyl) Peroxide and (CH3)3SiX
J. Am. Chem. Soc., 122, 1245-1246 (2000)
D. Sawada and M. Shibasaki
Enantioselective Total Synthesis of Epothilone A Using Multifunctional Asymmetric Catalyses
Angew. Chem. Int. Ed., 39, 209-213 (2000)
M. Shibasaki
Multifunctional Asymmetric Catalysis
Enantiomer, 4, 513-527 (2000)
S. Matsunaga, J. Das, J. Roels, E.M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, and M. Shibasaki.
Catalytic Enantioselective meso-Epoxide Ring Opening Reaction with Phenolic Oxygen Nucleophile Promoted by Gallium Heterobimetallic Multifunctional Complexes.
J. Am. Chem. Soc., 122, 2252-2260 (2000)
M. Takamura, K. Funabashi, M. Kanai, and M. Shibasaki
Asymmetric Reissert-type Reaction Promoted by Bifunctional Catalyst
J. Am. Chem. Soc., 122, 6327-6328 (2000)
Y.S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, and M. Shibasaki
Stable, Storable and Reusable Asymmetric Catalyst: a Novel La-linked-BINOL Complex for Catalytic Asymmetric Michael Reaction
J. Am. Chem. Soc., 122, 6506-6507 (2000)
Y. Hamashima, M. Kanai, and M. Shibasaki
Catalytic Enantioselective Cyanosilylation of Ketones
J. Am. Chem. Soc., 122, 7412-7413 (2000)
D. Sawada, M. Kanai, and M. Shibasaki
Enantioselective Total Synthesis of Epothilone A and B Using Multifunctional Asymmetric Catalysei
J. Am. Chem. Soc., 122, 10521-10532 (2000)
I. Sakurada, S. Yamasaki, M. Kanai, and M. Shibasaki
Dichlorotin Oxide-catalyzed New Direct Functionalization of Olefins: Synthesis of trans β-Azidohydrins and 1,2-Diols
Tetrahedron Lett., 41, 2415-2418 (2000)
M. Kanai, Y. Hamashima, and M. Shibasaki
Design of a New Bifunctional Asymmetric Catalyst from Carbohydrates: Application to Catalytic Asymmetric Cyanosilylation of Aldehydes and Acetophenone
Tetrahedron Lett., 41, 2405-2409 (2000)
M. Takamura, Y. Hamashima, H. Usuda, M. Kanai, and M. Shibasaki
A Catalytic Asymmetric Strecker-Type Reaction: Interesting Reactivity Difference between TMSCN and HCN
Angew. Chem. Int. Ed., 39, 1650-1652 (2000)
K. Ohori, S. Shimizu, T. Ohshima, and M. Shibasaki
Catalytic Asymmetric Synthesis of 19,20-Dihydroakuammicine
Chirality, 12, 401-403 (2000)
I. Schlemminger, Y. Saida, H. Groger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, and J. Martens
Concept of Improved Rigidity: How to Make Enantioselective Hydrophosphonylation of Cyclic Imines Catalyzed by Chiral Heterobimetallic Lanthanoid Complexes almost Perfect
J. Org. Chem., 65, 4818-4825 (2000)
M. Takamura, Y. Hamashima, H. Usuda, M. Kanai, and M. Shibasaki
A Catalytic Asymmetric Strecker-Type Reaction Promoted by Lewis Acid-Lewis Base Bifunctional Catalyst
Chem. Pharm. Bull, 48, 1586-1592 (2000)
S. Matsunaga, T. Ohshima and M. Shibasaki
Immobilization of asymmetric multifunctional catalysts on an insoluble polymer
Tetrahedron Lett., 41, 8473-8478 (2000)
N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, and M. Shibasaki
Direct Catalytic Asymmetric Aldol Reaction: Synthesis of Either syn- or anti-α β-Dihydroxy Ketones
J. Am. Chem. Soc., 123, 2466-2467 (2001)
T. Nemoto, T. Ohshima, K. Yamaguchi, and M. Shibasaki
Catalytic Asymmetric Epoxidaiton of Enones Using La-BINOL-Triphenylarsine Oxide Complex: Structural Determination of the Asymmetric Catalyst
J. Am. Chem. Soc., 123, 2725-2732 (2001)
T. Nemoto, T. Ohshima and M. Shibasaki
Enantioselective Total Syntheses of Novel PKC Activator (+)-Decursin and Its Derivatives Using Catalytic Asymmetric Epoxidation of an Enone
Tetrahedron Lett., 41, 9569-9574 (2001)
Y. Hamashima, D. Sawada, H. Nogami, M. Kanai, and M. Shibasaki
Highly Enantioselective Cyanosilylation of Aldehydes Catalyzed by a Lewis Acid-Lewis Base Bifunctional Catalyst
Tetrahedron, 57, 805-814 (2001)
N. Yoshikawa and M. Shibasaki
Direct Catalytic Asymmetric Aldol Reactions Promoted by Novel Heterobimetallic Catalysts Possessing Strong Bronsted Base: A New Strategy for the Development of Lewis Acid-Bronsted Base Bifunctinal Catalysts
Tetrahedron, 57, 2569-2579 (2001)
H. Nogami, S. Matsunaga, M. Kanai and M. Shibasaki
Enantioselective Strecker-Type Reaction Promoted by Polymer-Supported Bifunctional Catalyst
Tetrahedron Lett., 42, 279-283 (2001)
Y. Hamashima, M. Kanai and M. Shibasaki
Catalytic Enantioselective Cyanosilylation of Ketones: Improvement of Enantioselectivity and Catalyst Turn-Over by Ligand Tuning
Tetrahedron Lett., 42, 691-694 (2001)
S. Yamasaki, M. Kanai and M. Shibasaki
Novel Multiaction of Zr Catalyst: One-Pot Synthesis of β-Cyanohydrins from Olefins
J. Am. Chem. Soc., 123, 1256-1257 (2001)
H. Sasai, T. Arai, S. Watanabe and M. Shibasaki
Novel heterobimetallic asymmetric catalysis directing toward enzymatic function
Catalysis Today, 62, 17-22 (2001)
M. Shibasaki and M. Kanai
Multifunctional Asymmetric Catalysis
Chem. Pharm. Bull. 49, 551-524 (2001)
N. Kumagai, S. Matsunaga, N. Yoshikawa, T. Ohshima, and M. Shibasaki
Direct Catalytic Enantio- and Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex: A Practical Synthesis of syn-1,2-Diols
Org. Lett., 3, 1539-1542 (2001)
M.A. Arai, T. Arai, and H. Sasai
Design and Synthesis of the First Spiro Bis(isoxazoline) Derivatives as Asymmetric ligands
Org. Lett., 1, 1795-1798 (1999)
T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu, and H. Sasai
Immobilization of Heterobimetallic Multifunctional Asymmetric Catalyst
Org. Lett., 2, 4261 (2000)
M.A. Arai, M. Kuraishi, T. Arai, and H. Sasai
A New Asymmetric Wacker-Type Cyclization and Tandem Cyclization Promoted by Pd(II)-Spiro Bis(Isoxazorine) Catalyst
J. Am. Chem. Soc., 123, 2907-2908 (2001)
K. Yasuda, M. Shindo, and K. Koga
Enantioselective Michael Reaction of Ketone Lithium Enolates Using a Chiral Amine Ligand
Tetrahedron Lett., 37, 6343 (1996)
K. Sugasawa, M. Shindo, H. Noguchi, and K. Koga
Solution Structures of a Monodentate Chiral Lithium Amide in the Presence of Lithium Halide
Tetrahedron Lett., 37, 7377-7380 (1996)
T. Yamashita, D. Sato, T. Kiyoto, A. Kumar, and K. Koga
An Approach to Catalytic Asymmetric Deprotonation of 4-Substituted Cyclohexanones
Tetrahedron Lett., 37, 8195-8198 (1996)
K. Ishii, S. Aoki, and K. Koga
Enantioselective Methylation of the Lithium Enolate of 1-Tetralone Mediated by Chiral C2-Symmetric DMEU Derivatives
Tetrahedron Lett., 38, 563 (1997)
M. Toriyama, K. Sugasawa, M. Shindo, N. Tokutake, and K. Koga
Stereochemistry of Enantioselective Deprotonation of 4-Substituted Cyclohexanones by Chiral Bidentate Lithium Amides
Tetrahedron Lett., 38, 567-570 (1997)
K. Aoki and K. Koga
Enantioselective Deprotonation of 4-tert-Butylcyclohexanone by Fluorine-Containing Chiral Lithium Amides Derived from a-Phenethylamine
Tetrahedron Lett., 38, 2505-2506 (1997)
R. Shirai, D. Sato, K. Aoki, M. Tanaka, H. Kawasaki, and K. Koga
Stereoselective Reaactions. XXV. Enantioselective Deprotonation of Prochiral 4-Substituted Cyclohexanones by Chiral Chelated Lithium Amides
Tetrahedron, 53, 5963 (1997)
K. Yasuda, M. Shindo, and K. Koga
Construction of Contiguous Chiral Tertiary Carbon Centers by Enantioselective Michael Reaction of Ketone Lithium Enolates Using a Chiral Amine Ligand
Tetrahedron Lett., 38, 3531-3534 (1997)
D. Sato, H. Kawasaki, I. Shimada, Y. Arata, K. Okamura, T. Date, and K. Koga
Stereoselective Reactions. XXVI. Solution Structures of a Chiral Bidentate Lithium Amide in Relation to the Solvent-Dependent Enantioselectivities in Deprotonation Reaction
Tetrahedron, 53, 7191 (1997)
K. Tomioka, M. Okuda, K. Nishimura, S. Manabe, M. Kanai, Y. Nagaoka, and K. Koga
Structural Requirements of a Chiral Ligand for the Catalytic Asymmetric Addition of Thiophenol to α β Unsaturated Esters
Tetrahedron Lett., 39, 2141-2144 (1998)
T. Kumamoto and K. Koga
Enantioselective Horner-Wadsworth-Emmons Reaction Using Chiral Lithium 2-Aminoalkoxide
Chem. Pharm. Bull., 45, 753-755 (1997)
D. Sato, H. Kawasaki, and K. Koga
Stereoselective Reactions. XXVII. Solution Structures of a Chiral Tridentate Lithium Amide in Relation to Enantioselective Deprotonation of 4-tert-Butylcyclohexanone
Chem. Pharm. Bull., 45, 1399-1402 (1997)
J.-I. Matsuo and K. Koga
Enantioselective α Alkylation of Phenylacetic Acid Using a Chiral Bidentate Lithium Amide as a Chiral Auxiliary
Chem. Pharm. Bull., 45, 2122-2124 (1997)
P. Riviere and K. Koga
An Approach to Catalytic Enantioselective Protonation of Prochiral Lithium Enolates
Tetrahedron Lett., 38, 7589-7592 (1997)
K. Aoki, K. Tomioka, H. Noguchi, and K. Koga
Stereoselective Reactions. XXVIII. Effects of the Alkyl Group at the Amide Nitrogen of Chiral Bidentate Lithium Amides on Enantioselective Deprotonation Reaction
Tetrahedron, 53, 13641-13656 (1997)
T. Yamashita, D. Sato, T. Kiyota, A. Kumar, and K. Koga
Stereoselective Reactions. XXIX. Lithium-Hydrogen Interchange between Achiral Tridentate Lithium Amides and Chiral Bidentate Amines. An Approach to Catalytic Enantioselective Deprotonation
Tetrahedron, 53, 16987-16998 (1997)
H. Chatani, M. Nakajima, H. Kawasaki, and K. Koga
Chiral Bidentate Lithium Amides Having a Chiral Amide Nitrogen for Enantioselective Deprotonation of 4-tert-Butylcyclohexanone
Heterocycles, 46, 53-56 (1997)
古賀憲司、小田嶋和徳
キラル塩基を用いる不斉合成
薬学雑誌, 117, 800-8167 (1997)
M. Murakata, T. Yasukata, T. Aoki, M. Nakajima, and K. Koga
Stereoselective Reactions. XXX. Enantioselective Alkylation of the Lithium Enolates of Six-membered Cyclic Ketones Using Tetradentate Chiral Amines in the Presence of Lithium Bromide
Tetrahedron, 54, 2449-2458 (1998)
J.-I. Matsuo, S. Kobayashi, and K. Koga
Enantioselective Alkylation of Lactams and Lactones via Lithium Enolate Formation Using a Chiral Tetradentate Lithium Amide in the Presence of Lithium Bromide
Tetrahedron Lett., 39, 9723-9726 (1998)
Y. Yamashita, K. Odashima, and K. Koga
Construction of Chiral Quaternary Carbon Centers by Asymmetric Alkylation of Achiral Lithium Enolates Mediated by Chiral Tetradentate Ligands: Stoichiometric and Catalytic Approaches
Tetrahedron Lett., 40, 2803-2806 (1999)
M. Goto, K. Akimoto, K. Aoki, M. Shindo, and K. Koga
1,1,4,7,10,10-Hexamethyltriethylenetetramine: A Reagent to Enhance the Rate of Alkylation Reaction of the Lithium Enolate of 1-Tetralone with Alkyl Halides
Tetrahedron Lett., 40, 8129-8132 (1999)
Y. Yamashita, Y. Emura, K. Odashima, and K. Koga
Catalytic Asymmetric Protonation by a Chiral Tetraamine Ligand with Water as a Proton Source
Tetrahedron Lett., 41, 209-213 (2000).
M. Imai, A. Hagihara, H. Kawasaki, K. Manabe, and K. Koga
Stereoselective Reactions, Part 31. Catalytic Asymmetric Alkylation of Achiral Lithium Enolates Using a Chiral Tetradentate Amine in the Presence of an Achiral Bidentate Amine
Tetrahedron, 56, 179-185 (2000)
K. Aoki and K. Koga
Stereoselective Reactions. XXXII. Enantioselective Deprotonation of 4-tert-Butyulcyclohexanone by Fluorine-Containing Chiral Lithium Amides Derived from 1-Phenylethylamine and 1-(1-Naphthyl)ethylamine
Chem. Pharm. Bull., 48, 571-574 (2000)
M. Goto, K. Akimoto, K. Aoki, M. Shindo, and K. Koga
Rate Enhancement with High Ratio of the Monoalkylated Product to the Dialkylated Product in the Alkylation of the Lithium Enolate of 1-Tetralone with Reactive Alkyl Haalides
Chem. Pharm. Bull., 48, 1529-1531 (2000)
M. Toriyama, N. Tokutake, and K. Koga
Stereoselective Reactions. XXXIII. Design and Synthesis of Chiral Bidentate Amines Having a Bulky Group on the Chiral Carbon.
Chem. Pharm. Bull., 49, 330-334 (2001)
M. Toriyama, K. Sugasawa, S. Motohashi, N. Tokutake, and K. Koga
Stereoselective Reactions. XXXIV. Enantioselective Deprotonation of Prochiral 4-Substituted Cyclohexanones Using Chiral Bidentate Lithium Amides Having a Bulky Group Instead of a Phenyl Group on the Chiral Carbon.
Chem. Pharm. Bull., 49, 468-472 (2001)
(2)口頭発表
招待講演
福山 透
W.S. Johnson Symposium, ACS Annual Meeting (San Francisco, California) April 1997.
16th International Congress of Heterocyclic Chemistry, (Bozeman, Montana) August 1997.
Gordon Conference on Natural Products (New Hampshire, USA) July 1998.
8th Brazilian Meeting on Organic Synthesis (Sao Pedro, Brazil) 1998.
POSTECH Symposium (Pohang, South Korea) November 1998.
Novartis Lecture (Colorado State University, Fort Collins, Colorado) January 1999.
Lilly Lecture (Ohio State University, Columbus, Ohio) April 1999.
16th International Symposium on Synthesis in Organic Chemistry (Cambridge, England) July 1999.
Gordon Conference on Heterocyclic Compounds (Rhode Island, USA) July 2000.
MCR 2000-An International Conference on Multi Component Reactions, Combinatorial and related Chemistry (München, Germany) September 2000.
柴崎正勝
SFC-Rhone Poulenc Lectureship (France) 1997.
Warner Lambert Park-Davis Lecturer (Ohio State University, USA) 1997.
Büchi Lecturer (MIT, USA) 1999.
Bristol-Myers Squibb Lecturer (Harvard University, USA) 1999.
Syntex Distinguished Lecturer (Colorado State University, USA) 1999.
H.C. Brown Lecturer (Purdue University, USA) 1999.
BioMega Lecturer (University of Toronto, Canada) 2000.
UCLA/Amgen Lecturer (University of California, Los Angeles, USA) 2000.
Bristol-Myers Squibb Lecturer (University of California, Berkeley, USA) 2000.
Novartis Chemistry Lectureship (Novartis, Switzerland) 2000/2001.
Organic Synthesis Lecturer (University of California, Irvine, USA) 2001
その他多数
古賀憲司
IUPAC Symposium on Organic Chemistry (Sendai, Japan) August 1998.
American Chemical Society Annual Meeting (Boston, USA) August 1998.
The 5th Anglo-Norman Organic Chemistry Colloquim (Normandie, France) May 1999.
Workshop on Asymmetric Protonation and Deprotonation to Honor Prof. Dr. L. Duhamel (Normandie, France) May 1999.
Canadian Chemical Society Annual Meeting (Calgary, Canada) May 2000.
口頭講演
小林義久、藤本哲平、福山透
「インドロカルバゾール(+)-K252aの合成研究」
第40回天然有機化合物討論会、1998年10月、福岡
徳山英利、山下徹、M.T. Reding、鏑木洋介、福山透
「2-アルケニルチオアニリドのラジカル環化反応を用いた新規2,3-二置換インドール合成法とその応用」
第41回天然有機化合物討論会、1999年10月、名古屋
黒川利樹、福山透
「(+)-リセルグ酸の合成研究」
第31回複素環化学討論会、2000年10月、北九州
遠藤篤史、菅敏幸、福山透
「エクテナサイジン743の合成研究」
第75回有機合成シンポジウム、1999年6月、東京
黒澤渉、菅敏幸、福山透
「エフェドラジンAの合成研究」
第77回有機合成シンポジウム、2000年6月、東京
神戸美香、新井恵理、鈴木雅士、徳山英利、福山透
「FR-900482の合成研究」
第78回有機合成シンポジウム、2000年9月、京都
藤本哲平、北岡悠、家田茂、菅敏幸、福山透
「FR901483の合成研究」
第79回有機合成シンポジウム、2001年6月、東京
和泉延明、伊東哲志、福山透
「(-)--CP-263,114 (Phomoidride B)の全合成」
第42回天然有機化合物討論会、2000年11月、沖縄
H. Tokuyama, T. Ueda, M.T. Reding, S. Kobayashi, E.J. Zylstra, and T. Fukuyama,
“A Novel Synthesis of 2,3-Disubstituted Indoles and Its Application to Total Synthesis of Indole Alkaoids”
The 8th international Kyoto Conference on New Aspects of Organic Chemistry, Kyoto, July 2000.
その他多数
2.ポスター発表
T. Kan, Y. Hidai, A. Fujiwara, and T. Fukuyama
“Synthetic Study on Polyamine Toxins via 2-Nitrobenzenesulfonamide Protection/ Activation Strategies”
The 47th Gordon Research Conference on Natural Products Chemistry, July 1998, New Hampshire USA.
H. Tokuyama, S. Yokoshima, T. Yamashita, and T. Fukuyama,
“A Novel Ketone Synthesis by a Palladium-catalyzed Reaction of Thiol Esters and Organozinc Reagents”
The 5th International Symposium on Carbanion Chemistry, Sendai, August 1998.
H. Tokuyama, T. Yamashita, M. T. Reding, Y. Kaburagi, and T. Fukuyama,
“A Novel Synthesis of 2,3-Disubstituted Indoles by Radical Cyclization of 2-Alkenylthioanilides and Applications for Natural Product Synthesis”
The 48th Gordon Research Conference on Natural Products Chemistry, July 1999, New Hampshire USA.
T. Fujimoto, S. Ieda, T. Kan, and T. Fukuyama,
“Synthetic Studies on FR901483”
The 8th international Kyoto Conference on New Aspects of Organic Chemistry, Kyoto, July 2000.
S. Yokoshima, H, Tokuyama, and T. Fukuyama, T. Fukuyama,
“Total Synthesis of (+)-Gelsemine”
International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec. 2000.
A. Endo,, S. Tohma, T. Kan, and T. Fukuyama,
“Synthetic Studies on Ecteinascidin 743”
International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec. 2000.
T. Kurokawa and T. Fukuyama,
“Synthetic Studies on (+)-Lysergic Acid,”
International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec. 2000.
H. Tokuyama, T. Ueda, M.T. Reding, S. Kobayashi, E.J. Zylstra, and T. Fukuyama, T. Fukuyama, M. Kambe, M. Suzuki, H. Tokuyama,
“Novel Synthesis of 2,3-Disubstituted Indoles and Its Application to Total Synthesis of Indole Alkaloids”
International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec. 2000.
M. Suzuki, M. Kambe, E. Arai, T. Fukuyama, T. Fukuyama, M. Kambe, M. Suzuki, H. Tokuyama
“Total Synthesis of Optically Active FR900482 and Its Analogs”
International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, Dec. 2000.
N. Waizumi, T. Ito, Y. Hayashi, and T. Fukuyama
“Total Synthesis of (-)-CP-263,114 (Phomoidride B)
The 15th French-Japanese Symposium on Medicinal and Fine Chemistry, Nara, May 2001.
T. Yamashita, H. Tokuyama, N. Kawai, and T. Fukuyama
“Total Synthesis of Eudistomin C,”
The 10th International Symposium on Marine Natural Products, Okinawa, June 2001.
その他多数
(3)特許出願(国内 9 件)
福山透
「ポリアミン固相合成反応方法と固相反応担体」
特願平11-240361、平成11年8月26日
福山透
「インドロカルバゾール骨格の構築方法」
特願平11-52498、平成11年3月1日
福山透、徳山英利
「FR900482類縁体とその合成方法」
福山透、徳山英利
「光学活性 FR-900482およびその類縁化合物並びに合成中間化合物とその製造法」
特願2000-404281、平成12年12月14日
福山透、徳山英利
「ビンドリン合成中間体およびビンドリン合成中間体の合成方法」
特願2000-377199、平成12年12月12日
福山透、徳山英利
「置換アニリンから置換キノリンを製造する新規合成法」
特願2000-372508、平成12年12月7日
福山透
「(-)-ビンドリン類の不斉合成方法の改良」
特願2000-335349、平成12年11月2日
福山透、徳山英利、山下徹
「オキサチアゼピン環の合成方法」
福山透、徳山英利、山下徹
「ユーディストミン合成中間体およびその合成方法」
(4)受賞等
柴崎正勝 フルカ賞「Reagent of the Year, 1996」(スイス)受賞
笹井宏明 フルカ賞「Reagent of the Year, 1996」(スイス)受賞
柴崎正勝 エルセビア賞「Elsevier Award for Inventiveness in Organic Chemistry, 1997」(ベルギー)
柴崎正勝 日本薬学会賞(1999年)
柴崎正勝 Molecular Chirality Award(1999年)
飯田剛彦 第10回(1997年度) 有機合成化学協会「研究企画賞」
金井 求 第12回(1999年度)有機合成化学協会「研究企画賞」
徳山英利 第41回天然有機化合物討論会奨励賞
金井 求 平成13年度日本薬学会奨励賞
大嶋孝志 第13回(2000年度)有機合成化学協会「研究企画賞」
伊東哲志 第42回天然有機化合物討論会奨励賞
(5)その他特記事項
1. 多点制御型不斉触媒の市販化
·LLB錯体はTHF溶液としてFluka社より市販されている。また、空気中でも極めて安定な粉末錯体であるLa-linked-BINOL錯体がStrem社より近日市販されることが決定された。
2. 多点制御型不斉触媒の工業化への展開
·光学活性希土類錯体は、少量の水の存在下でも触媒活性を失わない安定な錯体であり、これらを用いる触媒的不斉合成が、近年工業スケールでも展開されている。
·LaK3tris(binaphthoxide) (LPB) (5 mol%)を触媒とする鎖状イミンのヒドロホスホニル化は北興化学工業株式会社により工業化されており、現在、シグマアルドリッチ社よりα-アミノホスホン酸とその鏡像異性体、計8種が市販されている。
·鐘淵化学工業株式会社により触媒的ニトロアルドール反応が工業化され、抗HIV活性が注目されているKNI-272の構成単位であるβ-アミノ酸が高いジアステレオ選択性で合成されている。
·ALB錯体を用いた触媒的不斉Michael反応は、イーライリリー社において1 kgスケールの反応へと展開されている。
·三共株式会社において触媒的不斉シアノシリル化を鍵工程とする抗糖尿病薬の鍵中間体合成プロセスの工業化が進められている。