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)


Visible-light-induced reductive coupling of arylacetylenes with benzothiazole sulfones
Tetsuya Sengoku, Haruka Iwama, Takuma Shimotori, Keisuke Fujimoto, Toshiyasu Inuzuka, Koki Matsune, Hidemi Yoda
The Journal of Organic Chemistry 2023, 88, 12776-12782. (DOI: 10.1021/acs.joc.3c01554)

The reductive coupling of alkyl or benzylic benzothiazole sulfones with arylacetylenes are performed in the presence of Hantzsch esters and K2CO3 under visible-light irradiation. The utility of this protocol is expanded to α-deuterative coupling using a deuterated Hantzsch ester, furnishing the corresponding alkenes with high deuterium incorporation.

Journal Information: Impact factor 3.6 (Q1, JCR 2023)


Total synthesis and structural confirmation of (±)-spirocollequins A and B
Keita Ichikawa, Toshiyasu Inuzuka, Hidemi Yoda and Tetsuya Sengoku
Tetrahedron Letters 2022, 107, 154109. (DOI: 10.1016/j.tetlet.2022.154109)

The first total synthesis of antiplasmodial isoindolinone alkaloids, spirocollequins A and B, has been accomplished. The proposed structures of spirocollequins have been supported through the comparison of spectroscopic properties of the synthetic samples with those of natural products as well as single-crystal X-ray diffraction analysis using a synthetic precursor of spirocollequin B.

Journal Information: Impact factor 1.8 (Q3, JCR 2022)


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)


A heavy-metal-free desulfonylative Giese-type reaction of benzothiazole sulfones under visible-light conditions
Tetsuya Sengoku, Daichi Ogawa, Haruka Iwama, Toshiyasu Inuzuka and Hidemi Yoda
Chemical Communications, 202157, 9858–9861. (DOI: 10.1039/D1CC03833H) 

A heavy-metal-free desulfonylative Giese-type reaction has been achieved by using Hantzsch ester as a photoreductant under blue light.

Journal Information: Impact factor 6.065 (Q1, JCR 2021)


Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams
Tetsuya Sengoku, Koki Makino, Ayumi Iijima, Toshiyasu Inuzuka and Hidemi Yoda
Beilstein Journal of Organic Chemistry,  2020, 16, 2769–2775. (DOI: 10.3762/bjoc.16.227) 

New synthetic methods for spirolactams bearing an α-methylene-γ-butyrolactone or its analogous methylene-lactam have been developed.

Journal Information: Impact factor 2.883 (Q2, JCR 2020)


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)

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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%.

Journal Information: Impact factor 5.837 (Q1, JCR 2020)