2024年10月11日 第53回複素環化学討論会で、ポスター発表を行います。
ChemistrySelect誌に掲載決定！
Asymmetric Allylation of Aldoxime Derivatives with β-Amidoallylboronate in Water and Its Application to Divergent Synthesis of N-Hydroxy-γ-lactam and 1,2-Oxazinan-6-one
Tetsuya Sengoku, Wataru Anze, Naoya Hasegawa, Yuta Mizutani, Asahi Kubota, Toshiyasu Inuzuka, and Hidemi Yoda
ChemistrySelect 2024, 9, e202400120. (DOI: 10.1002/slct.202400120)
A highly enantioselective amido–functionalized allylation of aldoxime derivatives was achieved in water using O-Boc oximes as substrates under Zn(OH)2-chiral aminophenol catalysis. The products could be transformed into N-hydroxy-γ-lactam or 1,2-oxazinan-6-one, through an acidic treatment or a protection-acidic treatment sequence, respectively.
Journal Information: Impact factor 2.1 (Q3, JCR 2023)
AsianJOC誌に掲載決定！
Copper sulfate-catalyzed asymmetric 1,4-addition of amido-functionalized allylboronates to maleimides in water
Tetsuya Sengoku, Takuto Kajihara, Mari Inaba and Hidemi Yoda
Asian Journal of Organic Chemistry 2022, 11, e202100773. (DOI: 10.1002/ajoc.202100773)
A new application of amido-functionalized allylboronates to asymmetric 1,4-addition in water has been developed. Extremely high enantioselective 1,4-addition was achieved by employing N-mesityl maleimide as a substrate under CuSO4/bis(oxazoline) catalysis, affording the adduct with >99% ee.
Journal Information: Impact factor 2.7 (Q2, JCR 2022)
有機合成化学協会誌に総合論文が掲載されました
アミド修飾したアリル化剤を利用するα-メチレン-γ-ブチロラクトンおよびα-メチレン-γ-ブチロラクタムの選択的合成
仙石哲也, 依田秀実
有機合成化学協会誌, 2021, 79, 829–838.
三好さん、津田さんの論文がTetrahedron誌に掲載決定！
Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
Tetsuya Sengoku, Ayako Miyoshi, Tamaki Tsuda, Toshiyasu Inuzuka, Masami Sakamoto, Masaki Takahashi and Hidemi Yoda
Tetrahedron, 2020, 76, 131252. (DOI: 10.1016/j.tet.2020.131252)
Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities.
Journal Information: Impact factor 2.457 (Q2, JCR 2020)
前川君、今村君、和田君の論文がAdv. Synth. & Catal.誌に掲載決定！
Zinc Hydroxide‐Catalyzed Asymmetric Allylation of Acetophenones with Amido‐Functionalized Allylboronate in Water
Tetsuya Sengoku, Ryunosuke Maegawa, Hiroki Imamura, Mitsuo Wada and Hidemi Yoda
Advanced Synthesis & Catalysis, 2020, 362, 2397-2418. (DOI: 10.1002/adsc.202000195)
Enantioselective reaction of water‐stable amido‐functionalized allylboronates with acetophenone derivatives in water is reported. The reaction was catalyzed with zinc hydroxide and a didecylamino‐functionalized chiral aminophenol reagent, affording a variety of homoallylic alcohols in up to 99% yield. The enantiomeric excess of the product reached up to 98%.
Journal Information: Impact factor 5.837 (Q1, JCR 2020)
池田君、阿井君の論文がOrganic & Biomolecular Chemistry誌に掲載決定！
Indium− and zinc−catalyzed enantioselective amide propargylation of aldehydes with stannylated allenyl amides
Tetsuya Sengoku, Ikuhei Ikeda, Keisuke Ai, Masaki Takahashi and Hidemi Yoda
Organic & Biomolecular Chemistry, 2019, 17, 2614-2618. (DOI: 10.1039/C9OB00040B)
A highly enantioselective allylation of aldehydes with newly prepared stannyl allenyl amides has been achieved using catalytic amounts of InCl3, ZnCl2 and a BINOL derivative.
Journal Information: Impact factor 3.412 (Q1, JCR 2019)
杉山君、神谷君、前川君の論文がEJOC誌に掲載決定！
Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Enantioselective Addition to Isatins
Tetsuya Sengoku, Akihiro Sugiyama, Yuta Kamiya, Ryunosuke Maegawa, Masaki Takahashi and Hidemi Yoda
European Journal of Organic Chemistry, 2017, 1285-1288. ()
A new catalytic system that enables the enantioselective tin-free “amide allylation” of isatins is developed with the aid of a newly prepared (β-amidoallyl)boronate.
Journal Information: Impact factor 3.068 (Q2, JCR 2015)
小久保さんの論文がOBC誌に掲載決定！
Indium-catalysed Amide Allylation of α-Iminoamide: Highly Enantioselective Synthesis of Amide Functionalised α-Methylene-γ-butyrolactams
Tetsuya Sengoku, Kana Kokubo, Masami Sakamoto, Masaki Takahashi and Hidemi Yoda
Organic & Biomolecular Chemistry, 2017, 15, 320-323. (DOI: 10.1039/C6OB02506D)
A highly enantioselective amide allylation of α-iminoamides has been achieved using catalytic amounts of InCl3, ZnCl2 and a BINOL derivative.
Journal Information: Impact factor 3.559 (Q1, JCR 2015)
Publication (~2016)
＊2008年以降の論文のタイトルは掲載論文webサイトにリンクしています。
- Indium-catalyzed Amide Allylation of N-carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-reclosure
Tetsuya Sengoku, Yusuke Murata, Yuwa Aso, Ai Kawakami, Toshiyasu Inuzuka, Masami Sakamoto, Masaki Takahashi and Hidemi Yoda, Organic Letters 2015, 17, 5846-5849.
- Synthesis of New Chiral Lactam–fused Pyridine Derivatives
Tetsuya Sengoku, Yusuke Murata, Chihiro Suzuki, Masaki Takahashi and Hidemi Yoda, RSC Advances 2015, 5, 73562-73565.
- Gap−filling Functionality of Energy Transmitter on Cascade Energy Transfer in a Unimolecular Anthracene/perylene/rhodamine System
Masaki Takahashi, Yuki Numata, Michiki Ui, Toshiyasu Inuzuka, Tetsuya Sengoku and Hidemi Yoda, Tetrahedron Letters, 2015, 56, 430-433.
- Developments in the Synthesis of 3-Acyltetramic Acid Natural Products, in Studies in Natural Products Chemistry (Bioactive Natural Products) ed. by Atta-ur-Rahman
Hidemi Yoda, Masaki Takahashi and Tetsuya Sengoku, Elsevier,2015, 46, 99-131. - Synthesis and Spectral Properties of Perylene–rhodamine Dyads with Lipophilic Dendritic Auxiliaries
Masaki Takahashi, Michiki Ui, Toshiyasu Inuzuka Tetsuya Sengoku and Hidemi Yoda, Tetrahedron, 2014,70, 9175-9182.
- Catalytic Amide Allylation of α-ketoester: Extremely High Enantioselective Synthesis of ester functionalised α-methylene-γ-butyrolactones
Masaki Takahashi, Yusuke Murata, Masahiro Ishida, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, and Hidemi Yoda, Organic & Biomolecular Chemistry, 2014, 12, 7686-7689.
- Novel Chiral Tetramic Acid–derived Diols: Organocatalytic Facile Synthesis and Unique Structural Properties
Tetsuya Sengoku, Kosuke Suzuki, Ken Nakayama, Fumitoshi Yagishita, Masami Sakamoto, Masaki Takahash, and Hidemi Yoda, RSC Advances 2014, 4, 30775-30779.
- Catalytic Enantioselective Amide Allylation of Isatins and Its Application to the Synthesis of 2–Oxindole Derivatives Spiro–Fused to α-Methylene-γ-Butyrolactone Functionality
Masaki Takahashi, Yusuke Murata, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, and Hidemi Yoda, Chemistry – A European Journal 2014, 20, 11091-11100.
- Construction of Spiro-Fused 2-Oxindole/ α-Methylene-γ-Butyrolactone Systems with Extremely High Enantioselectivity via Indium-Catalyzed Amide Allylation of N-Methyl Isatin
Yusuke Murata, Masaki Takahashi, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, and Hidemi Yoda, Organic Letters, 2013, 15, 6182-6185.
- Invited review for a special issue on “New aspects in natural product synthesis: methodology and strategy”
Evolution of the Total Syntheses of Batzellasides, the First Marine Piperidine Iminosugar.
Tetsuya Sengoku, Jolanta Wierzejska, Masaki Takahashi and Hidemi Yoda, Natural Product Communications 2013, 8, 1011-1019.
- Invited article for a special issue on “New aspects in natural product synthesis: methodology and strategy”
Synthetic approach toward α-aminomethyl-γ-butyrolactones from β-lactam synthons elaborated by SmI2-mediated reductive coupling reactions.
Masaki Takahashi, Takahiro Sudo, Yusuke Murata, Tetsuya Sengoku and Hidemi Yoda, Natural Product Communications 2013, 8, 889-896.
- A new approach toward total synthesis of (+)-batzellaside B
Jolanta Wierzejska, Shin-ichi Motogoe, Yuto Makino, Tetsuya Sengoku, Masaki Takahashi and Hidemi Yoda, Beilstein Journal of Organic Chemistry 2012, 8, 1831-1838.
- First Total Synthesis of Epicoccarine A via O– to C-Acyl Rearrangement Strategy
Yasuaki Ujihara, Ken Nakayama, Tetsuya Sengoku, Masaki Takahashi, and Hidemi Yoda, Organic Letters 2012, 14, 5142-5145.
- First total synthesis and absolute stereochemical assignment of vittarilide-A, an antioxidant extractive component isolated from Vittaria anguste-elongata Hayata
Masaki Takahashi, Yusuke Murata, Yuki Hakamata, Kohei Suzuki, Tetsuya Sengoku and Hidemi Yoda, Tetrahedron, 2012, 68, 7997-8002.
- A Synthetic Approach to Diverse 3-Acyltetramic Acids via O– to C-Acyl Rearrangement and Application to the Total Synthesis of Penicillenol Series
Tetsuya Sengoku, Yuta Nagae, Yasuaki Ujihara, Masaki Takahashi, and Hidemi Yoda, The Journal of Organic Chemistry, 2012, 77, 4391-4401.
- Synthesis of novel mucic acid 1,4-lactone methyl ester 3-O-ferulate related to an extractive component isolated from the peels of Citrus sudachi
Tetsuya Sengoku, Yusuke Murata, Hiromi Mitamura, Masaki Takahashi, and Hidemi Yoda, Tetrahedron Lett. 2012, 53, 435-437.
- Synthesis of lipophilic bisanthracene fluorophores: versatile building blocks toward the synthesis of new light-harvesting dendrimers
Masaki Takahashi, Ayato Yamamoto, Toshiyasu Inuzuka, Tetsuya Sengoku, and Hidemi Yoda, Tetrahedron 2011, 67, 9484-9490.
- New Synthetic Methodology toward Macrolides/Macrolactams via Palladium-Catalyzed Carbon-Heteroatom Bond-Forming Reactions
Tetsuya Sengoku, Tomoya Hamamatsu, Toshiyasu Inuzuka, Masaki Takahashi, and Hidemi Yoda, Synlett, 2011, 1766-1768.
- First stereoselective synthesis of penicillenol A1 via novel O– to C-acyl rearrangement of O-acyltetramic acid
Tetsuya Sengoku, Jolanta Wierzejska, Masaki Takahashi and Hidemi Yoda, Synlett 2010, 2944-2946.
- Azetidine and its Derivatives, in Heterocycles in Natural Product Synthesis, ed, by Krishna C. Majumdar and Shital K. Chattopadhyay
Hidemi Yoda, Masaki Takahashi, and Tetsuya Sengoku, WILEY-VCH, 2011, 41-61.
- Extremely High Regio- and Stereoselective C-C Bond Formation of Substituted γ-hydroxylactams: Synthesis of Macronecines Based on Their Structural Duality
Tetsuya Sengoku, Takamasa Suzuki, Tatsuro Kakimoto, Masaki Takahashi and Hidemi Yoda, Tetrahedron, 2009, 65, 2415-2423.
- New Asymmetric Strategy for the Total Synthesis of Naturally Occurring (+)-Alexine and (-)-7-Epi-alexine
Masaki Takahashi, Tetsuya Maehara, Tetsuya Sengoku, Norifumi Fujita, Kunihiko Takabe and Hidemi Yoda, Tetrahedron, 2008, 64, 5254-5261. - Mechanistic Investigation of Energy Transfer in Perylene-cored Anthracene Dendrimers
Masaki Takahashi, Hironao Morimoto, Kentaro Miyake, Hideki Kawai, Yoshihisa Sei, Kentaro Yamaguchi, Mitsuji Yamashita, Tetsuya Sengoku and Hidemi Yoda, New Journal of Chemistry, 2008, 32, 547-553.
