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Synthetic Organic Chemistry Laboratory
Visible-Light-Induced Desulfurative Coupling of Alkyl Benzothiazolyl Sulfides with Electron-Deficient Alkenes/Alkynes: Dual Role of Base-Activated Hantzsch Ester
Tetsuya Sengoku, Koki Matsune, Takuma Shimotori, Nagisa Kikuchi, Haruto Hijikata, Shun Nishioka, and Reo Takahashi
ChemCatChem, 2025, 17, e202401427. (DOI: 10.1002/cctc.202401427) Open Access
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The Hantzsch ester anion acts not only as a photoreductant in the catalyst-free desulfurative coupling of alkyl benzothiazolyl sulfides with alkenes/alkynes, but also as a sacrificial reductant in an alternative organocatalytic reaction. The utility of this protocol is expanded to radical C-glycosylation, which includes a protective group-free substrate.
ChemRxiv, DOI:10.26434/chemrxiv-2024-bqs8z
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)
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.
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)
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)
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)
Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Amide Allylation of N-Carbonyl Imides
Tetsuya Sengoku, Yuta Kamiya, Ai Kawakami, Masaki Takahashi and Hidemi Yoda
European Journal of Organic Chemistry, 2017, 6096-6098. ()
β-Amido allylboronates showed sufficient nucleophilicity toward imides in the presence of catalytic zinc bromide and basic additives, affording excellent yields of azaspiro-γ-lactones through a ring opening-reclosure process on a gram scale.
Journal Information: Impact factor 2.834 (Q2, JCR 2016)
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)
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)