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.

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.

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.

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, 2020362, 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%.

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, 201917, 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.

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. (DOI: 10.1002/ejoc.201601612)

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。

  • 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.