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Synthetic Organic Chemistry

Recent Selected Publications (Prof. Kei Takeda)

• Chirality Transfer in Brook Rearrangement-Mediated SE2’ Solvolytic Protonation and Its Use in Estimation of the Propensity for Racemization of the a-Lithiocarbanions of the Substituents
  Michiko Sasakia, Misato Fujiwaraa, Yuri Kotomoria, Masatoshi Kawahatab, Kentaro Yamaguchi, Kei Takeda
  Tetrahedron in press.
• Synthetic Potential of Configurationally Unstable Chiral Carbanions
  Michiko Sasaki, Kei Takeda
  J. Synth. Org. Chem., Jpn. 71, 136-148, (2013).
• Synthetic Potential of Configurationally Unstable Chiral Carbanions
  Michiko Sasaki, Kei Takeda
  SYNLETT (ACCOUNT, invited), 23, 2153-2164.
• Enantioselective Trapping of an a-Chiral Carbanion of Acyclic Nitrile by a Carbon Electrophile
  Michiko Sasaki, Tomo Takegawa, Hidaka Ikemoto, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Chem. Commun. 48, 2897–2899 (2012).
• DISCUSSION ADDENDUM FOR: [3 + 4] Annulation Using a [β-(Trimethylsilyl)acryloyl]silane and the Lithium Enolate of an α,β-Unsaturated Methyl Ketone: (1R,6S,7S)-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo[5.4.0]undec-4-en-2-one
  Kei Takeda, Michiko Sasaki
  Org. Synth. 89, 267–273 (2012); Original Article: Org. Synth. 76, 199 (1999).
• Regio- and Stereoselective Multisubstituted Enol Ester Synthesis
  Noriko Okamoto, Yoshihisa Miwa, Hideki Minami, Kei Takeda, Reiko Yanada
  J. Org. Chem. 76, 9133–9138 (2011).
• One-Pot Approach to 2,3-Disubstituted-2,3-dihydro-4-quinolones from 2-Alkynylbenzamides
  Noriko Okamoto, Kei Takeda, Minoru Ishikura, Reiko Yanada
  J. Org. Chem. 76, 9139–9143 (2011).
• Steric Course of the Electrophilc Substitution of a Lithiocarbanion Generated from (S,E)-1-Phenylbut-2-en-1-yl Diisopropylcarbamate and Solvent Effects
  Hidaka Ikemoto, Michiko Sasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Eur. J. Org. Chem. 2011, 6553–6557.
• Enantioselective Synthesis of Siloxyallenes from Alkynoyl Silanes by Reduction and a Brook Rearrangement and Their Subsequent Trapping in a [4+2] Cycloaddition
  Michiko Sasaki, Yasuhiro Kondo, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Angew. Chem. Int. Ed. 50, 6375–6378 (2011) (Selected by Angewandte Chemie as a Very Important Paper).
  
• Platinum-Catalyzed One-Pot Tandem Synthesis of Indoles and Isoquinolines via Sequential Rearrangement of Amides and Aminocyclization
  Noriko Okamoto, Kei Takeda, Reiko Yanada
  J. Org. Chem. 75, 7615–7625 (2010).
• Solvent Effects on the Steric Course of [2,3]-Wittig Rearrangement of (S,E)-(3-(allyloxy)prop-1-ene-1,3-diyl)dibenzene and Its Derivatives
  Hidaka Ikemoto, Michiko Sasaki, Kei Takeda
  Eur. J. Org. Chem. 2010, 6643–6650.
• Platinum-Catalyzed Synthesis of Indoles and Isoquinolines from 2-Alkynylarylamides
  Noriko Okamoto, Yoshihisa Miwa, Hideki Minami, Kei Takeda, Reiko Yanada
  Synfacts, 2010 (3), 283-283 (2010).
• Formal Total Syntheses of (+)-Prelaureatin and (+)-Laurallene by Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation
  Michiko Sasaki, Kazuhisa Oyamada, Kei Takeda
  J. Org. Chem. 75, 3941–3943 (2010).
• Development of Epoxysilane Rearrangement and its Application to Chirality Transfer
  Michiko Sasaki, Hidaka Ikemoto, and Kei Takeda
  Heterocycles, 78, 2919-2941 (2009) (invited).
• One-pot Tandem Concise Synthesis of Indoles and Isoquinolines from Amides
  Noriko Okamoto, Yoshihisa Miwa, Hideki Minami, Kei Takeda, and Reiko Yanada
  Angew. Chem. Int. Ed. 48, 9693-9696 (2009).

• One-pot Concise Syntheses of Benzimidazo[2,1-a]isoquinolines by Microwave-Accelerated Tandem Process
  Noriko Okamoto, Keisuke Sakurai, Minoru Ishikura, Kei Takeda, Reiko Yanada
  Tetrahedron Lett. 50, 4167-4169 (2009).
  
• [2,3]-Wittig Rearrangement of Enantiomerically Enriched 3-Substituted 1-Propenyloxy-1-phenyl-2-propen-1-yl Carbanions: Effect of Heteroatoms and Conjugating Groups on Planarization of an a-Oxy-Benzylcarbanion Through a Double Bond
  Michiko Sasaki, Hidaka Ikemoto, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Chem. Eur. J. 15, 4663-4666 (2009).
• Stereoselective Brook Rearrangement-Mediated S_E2' Protonation of a-Hydroxy Allyl Silanes
  Michiko Sasaki, Yuri Shirakawa, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Chem. Eur. J. 15, 3363-3366 (2009).
• Diastereoselective Brook Rearrangement-Mediated [3 + 4] Annulation: Application to a Formal Synthesis of (+)-Laurallene
  Michiko Sasaki, Azusa Hashimoto, Koudai Tanaka, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Org. Lett.10, 1803-1806 (2008).
• Chirality Transfer from Epoxide to Carbanion: Base-Induced Alkylation of O-Carbamoyl Cyanohydrins of b-Silyl-a,b-epoxyaldehyde
  Michiko Sasaki, Eiji Kawanishi, Yuri Shirakawa, Masatoshi Kawahata, Hyuma Masu, Kentaro Yamaguchi, Kei Takeda
  Eur. J. Org. Chem. 2008, 3061-3064.
• A novel Series of Parenteral Cephalosporins Exhibiting Potent Activities Against Both Pseudomonas Aeruginosa and Other Gram-Negative Pathogens. Part 2: Synthesis and Structure−Activity Relationships
  Kenji Yamawaki, Takashi Nomura, Tatsuro Yasukata, Norihiko Tanimoto, Koichi Uotani, Hideaki Miwa, Yoshinori Yamano, Kei Takeda, and Yasuhiro Nishitani
  Bioorg. Med. Chem. 16, 1632-1647 (2008).
• A Novel Series of Parenteral Cephalosporins Exhibiting Potent Activities Against Pseudomonas Aeruginosa and Other Gram-Negative Pathogens: Synthesis and Structure−Activity Relationships
  Kenji Yamawaki, Takashi Nomura, Tatsuro Yasukata, Koichi Uotani, Hideaki Miwa,Kei Takeda, Yasuhiro Nishitani
  Bioorg. Med. Chem. 15, 6716-6732 (2007).
• Development of New Synthetic Reactions Utilizing Charactristics of Silicon Atom
  Michiko Sasaki, Kei Takeda
  Chemistry and Education 55, 518-521 (2007).
• Development of New Synthetic Reactions Featuring Tandem Carbon-Carbon Bond Formation
  Kei Takeda
  YAKUGAKUZASSHI 127, 1399-1418 (2007).
• Stereocontrolled Construction of Seven-Membered Carbocycles Using a Combination of Brook Rearrangement-Mediated [3 + 4] Annulation and Epoxysilane Rearrangement
  Yoshio Nakai, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  J. Org. Chem. 72, 1379-1387 (2007).
• Tandem Epoxysilane Rearrangement/Wittig-Type Reactions Using γ-Phosphinoyl- and γ-Phosphonio-α,β-epoxysilane
  Michiko Sasaki, Mai Horai, Kei Takeda
  Tetrahedron Lett. 47, 9271-9273 (2006).
• Epoxysilane Rearrangement: Mechanistic Studies and Synthetic Applications
  Michiko Sasaki, Kei Takeda
  J. Synth. Org. Chem., Jpn. 64, 1148-1158 (2006).
• Epoxysilane Rearrangement Induced by a Carbanion Generated by Conjugate Addition of Enolates of Chloroacetate and α-Chloroacetamides: Formation of Functionalized Cyclopropane Derivatives.
  Noriko Okamoto, Michiko Sasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda
  Org. Lett. 8, 1889-1891 (2006).
• Asymmetric [2,3]-Wittig Rearrangement Induced by a Chiral Carbanion Whose Chirality Was Transferred from an Epoxide
  Michiko Sasaki, Mariko Higashi, Hyuma Masu, Kentaro Yamaguchi, and Kei Takeda
  Org. Lett. 7, 5913-5915 (2005).
• Nitrile Anion Cyclization with Epoxysilanes Followed by Brook Rearrangement/Ring-Opening of Cyclopropane Nitriles/Alkylation
  Seigo Okugawa, Hyuma Masu, Kentaro Yamaguchi, and Kei Takeda
  J. Org. Chem. 70, 10515-10523 (2005).
• Reaction of δ-Silyl-γ,δ-epoxy-α,β-unsaturated Acylsilanes with Cyanide Ion: Possibility of the Formation of Silicate Intermediate in Anion-Induced Ring-Opening of Epoxysilanes
  Koudai Tanaka, Hyuma Masu, Kentaro Yamaguchi, Kei Takeda
  Tetrahedron Lett. 46, 6429-6432 (2005).
• Ab initio MO Study on [3 + 2] Annulation Using β-Phenylthio-acryloylsilanes with Alkyl Methyl Ketone Enolates and its Through-Space/Bond Interaction Analysis
  Yuuichi Orimoto, Kazunari Naka, Kei Takeda, Yuriko Aoki
  Org. Biomol. Chem. 2005, 3, 2244-2249.
• γ-p-Toluenesulfonyl-α,β-epoxysilane: A New and Practical Acrolein β-Anion Equivalent
  Michiko Sasaki, Kei Takeda
  Org. Lett. 6, 4849-4851 (2004).
• Formation of Functionalized Carbocycles via Base-Promoted Ring-Opening/Brook Rearrangement/Allylic Alkylation of γ-Silyl-β,γ-epoxybutanenitrile Followed by Nitrile Anion Cyclization with Bis-Electrophiles
  Tatsuya Matsumoto, Hyuma Masu, Kentaro Yamaguchi, and Kei Takeda
  Org. Lett. 6, 4367-4369 (2004).
• Two-Fold Brook Rearrangement-Mediated Tandem Reactions of δ-Silyl-γ,δ-epoxy-α,β-unsaturated Acylsilanes with a Cyanide Ion
  Koudai Tanaka, and Kei Takeda
  Tetrahedron Lett. 45, 7859-7861 (2004).
• Nitrile Anion Cyclization with Epoxysilanes Followed by Brook Rearrangement/Ring-Opening of Cyclopropane Nitriles/Alkylation
  Seigo Okugawa, and Kei Takeda
  Org. Lett. 6, 2973-2975 (2004).
• Stereoselective Construction of Eight-Membered Oxygen Heterocycles by Brook Rearrangement-Mediated [3 + 4] Annulation
  Yuji Sawada, Michiko Sasaki, Kei Takeda
  Org. Lett. 6, 2277-2279 (2004).
• Tandem Base-Promoted Ring-Opening/Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehyde: Scope and Mechanism
  Michiko Sasaki, Eiji Kawanishi, Yoshio Nakai, Tatsuya Matsumoto, Kentaro Yamaguchi, Kei Takeda
  J. Org. Chem. 68, 9330-9339 (2003).
• A New Strategy for Construction of Eight-Membered Carbocycles by Brook Rearrangement Mediated [6 + 2] Annulation
  Kei Takeda, Hidekazu Haraguchi, Yasushi Okamoto
  Org. Lett. 5, 3705-3707 (2003).
• Tandem Base-Promoted Ring-Opening/Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes
  Kei Takeda, Eiji Kawanishi, Michiko Sasaki, Yuji Takahashi, Kentaro Yamaguchi
  Org. Lett. 4, 1511-1514 (2002).
• Stereoselective Construction of Eight-Membered Carbocycles by Brook Rearrangement-Mediated [3 + 4] Annulation
  Kei Takeda, Yuji Sawada, Koichi Sumi
  Org. Lett. 4, 1031-1033 (2002).
• [3 + 2] Annulation of β-Heteroatom-Substituted α,β-Unsaturated Acylsilanes with Methyl Ketone Enolates: Scope and Investigation of the Reaction Course
  Kei Takeda, Kenji Yamawaki, Noriaki Hatakeyama
  J. Org. Chem. 67, 1786-1794 (2002).
  
• Synthesis of the Tricyclic Skeleton of Cyathins Using Brook Rearrangement-Mediated [3 + 4] Annulation
  Kei Takeda, Daisuke Nakane, Mika Takeda
  Org. Lett. 2, 1903-1905 (2000).
• Reaction of Acylsilanes with Potassium Cyanide: Brook Rearrangement under Phase-Transfer Catalytic Conditions.
  Kei Takeda, Yuji Ohnishi
  Tetrahedron Lett. 41, 4169-4172 (2000).
• Reaction of Silyl Thioketones with Lithium Diethylphosphite: First Observation of Thia-Brook Rearrangement.
  Kei Takeda, Koichi Sumi, Susumu Hagisawa
  J. Organomet. Chem. 611, 449-454 (2000).
• Facile Construction of a Tricyclo[5.3.0.0^1,4]decenone Ring System by the Brook Rearrangement-Mediated [3 + 4] Annulation.
  Kei Takeda, Yasuhiro Ohtani
  Org. Lett. 1, 677-679 (1999).
• Enantioselective Reduction of α,β-Unsaturated Acylsilanes by Chiral Lithium Amides.
  Kei Takeda, Yuji Ohnishi, Toru Koizumi
  Org. Lett. 1, 237-239 (1999).
• Formation of Four- to Six-Membered Carbocycles by Tandem Brook Rearrangement-Intramolecular Michael Reaction.
  Kei Takeda, Tadashi Tanaka
  Synlett 1999, 705-708.
• [3 + 4] Annulation Using (β-(Trimethylsilyl)acryloyl)silane and Lithium Enolate of α,β-Unsaturated Methyl Ketone: (1R*,6R*,7R*-4-(tert-Butyldimethylsiloxy)-6-(trimethylsilyl)bicyclo[5.4.0]undec-4-en-2-one.
  Kei Takeda, Akemi Nakajima, Mika Takeda, Eiichi Yoshii, Jing Zhang, and R. K. Boeckman, Jr.
  Org. Synth. 76, 199-213 (1999).
• Synthesis of 4-Hydroxy-2-cyclopentenone Derivatives by [3 + 2] Annulation of β-Heteroatom-Substituted Acryloylsilanes and Lithium Enolate of Methyl Ketones.
  Kei Takeda, Yasuhiro Ohtani, Emi Ando, Ken-ichi Fujimoto, Eiichi Yoshii, and Toru Koizumi
  Chem. Lett. 1998, 1157-1158.
• Comparing α-Carbanion-Stabilizing Ability of Substituents Using the Brook Rearrangement.
  Kei Takeda, Haruka Ubayama, Ayako Sano, Eiichi Yoshii, Toru Koizumi
  Tetrahedron Lett. 39, 5243-5246 (1998).
• [3 + 4] Annulation of α,β-Unsaturated Acylsilanes with Enolates of α,β-Unsaturated Methyl Ketones: Scope and Mechanism.
  Kei Takeda, Akemi Nakajima, Mika Takeda, Yasushi Okamoto, Taku Sato, Eiichi Yoshii, Toru Koizumi, and Motoo Shiro
  J. Am. Chem. Soc. 120, 4947-4959 (1998).
• Asymmetric Reductive Cyclization Using the Intramolecular Conjugate Addition of Enolates onto α,β-Unsaturated Sulfoxides.
  Hiroki Yoshizaki, Tadashi Tanaka, Eiichi Yoshii, Toru Koizumi, Kei Takeda
  Tetrahedron Lett. 39, 47-50 (1998).
• Intramolecular C-H Insertion Reactions of Acetoxy Fischer Carbene Complexes.
  Kei Takeda, Yasushi Okamoto, Akemi Nakajima, Eiichi Yoshii, Toru Koizumi
  Synlett 1997, 1181-1183 (1997).
• Synthesis of Clavulones (Claviridenones) via [3 + 2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone.
  Kei Takeda, Kanji Kitagawa, Ichiro Nakayama, Eiichi Yoshii
  Synlett 1997, 251-252 (1997).
• Low-Temperature Oxyanion-Accelerated Vinylcyclopropane-Cyclopentene Rearrangement. Reacton of 2-(2-(Trimethylsilyl)ethenyl)cyclopropyl Acetates with Methyl Lithium.
  Kei Takeda, Keiki Sakurama, Eiichi Yoshii
  Tetrahedron Lett. 38, 3257-3260 (1997).
• BF₃･Et₂O-Mediated Intramolecular Allylstannane-Ketone Cyclizations: Formation of Bicyclo[4.1.0]hept-4-en-1-ols from 5-(Tributylstannyl)-3-cycloheptenones
  Kei Takeda, Akemi Nakajima, Eiichi Yoshii
  Synlett 1996, 753-754 (1996).
• New [3 + 4] Annulation. Reactions of (β-(Trimethylsilyl)acryloyl)silanes with the Lithium Enolates of α,β-Unsaturated Methyl Ketones.
  Kei Takeda, Mika Takeda, Akemi Nakajima, Eiichi Yoshii
  J. Am. Chem. Soc. 117, 6400-6401 (1995).
• Intramolecular Julia Condensation for the Construction of 15- and 14-membered Carbocycles in Terpestacin and Sarcophytol A.
  Kei Takeda, Akemi Nakajima, Eiichi Yoshii
  Synlett 1995, 249-250 (1995).
• Diels-Alder Reaction of α-Substituted Acrylates and α-(Methylene)lactones: Conformation of Dienophiles and Endo/Exo Selectivity.
  Kei Takeda, Ikuhiro Imaoka, Eiichi Yoshii
  Tetrahedron 1994, 10839-10848.
• A Short Synthesis of (±)-Untenone A, a Marine Sponge Cyclopentenone.
  Kei Takeda, Ichiro Nakayama, Eiichi Yoshii
  Synlett 1994, 178-178 (1994).
• Reaction of β-Heteroatom-Substituted α,β-Unsaturated Acylsilanes with Ketone Enolates: A New [3 + 2] Annulation Based on Brook Rearrangement.
  Kei Takeda, Masato Fujisawa, Tomoko Makino, Eiichi Yoshii, Kentaro Yamaguchi
  J. Am. Chem. Soc. 115, 9351-9352 (1993).
• Formation of 1,2-Cyclopropanediols in the Reaction of Acylsilanes with Ketone Enolates.
  Kei Takeda, Junko Nakatani, Hitoshi Nakamura, Koichi Sako, Eiichi Yoshii, Kentaro Yamaguchi
  Synlett 1993, 841-843 (1993).