Faculty Profiles - ISHIHARA Kazuaki

Papers - ISHIHARA Kazuaki

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Catalyst-Substrate Helical Character Matching Determines the Enantioselectivity in the Ishihara-Type Iodoarenes Catalyzed Asymmetric Kita-Dearomative Spirolactonization International coauthorship

Hanliang Zheng, Liu Cai, Ming Pan, Muhammet Uyanik, Kazuaki Ishihara, Xiao-Song Xue

Journal of the American Chemical Society Vol. 145 2023.4

Catalytic Site‐, Diastereo‐, and Enantioselective Cascade Iodocyclization of 2‐Geranylarenols Open Access

Yasutaka Tsuji, Kazumasa Kon, Takahiro Horibe, Kazuaki Ishihara

Chemistry – An Asian Journal Vol. 18 ( 7 ) 2023.4

Enantioselective aromatic Claisen rearrangement of allyl 2-naphthyl ethers catalyzed by π–Cu(<scp>ii</scp>) complexes Open Access

Lu Yao, Kazuki Takeda, Kaori Ando, Kazuaki Ishihara

Chemical Science Vol. 14 ( 9 ) page： 2441 - 2446 2023.3

Bulky magnesium(II) and sodium(I) bisphenoxide catalysts for chemoselective transesterification of methyl (meth)acrylates Open Access

Xue Zhao, Manussada Ratanasak, Kazumasa Kon, Jun-ya Hasegawa* and Kazuaki Ishihara*

Chemical Science Vol. 14 ( 3 ) page： 566 - 572 2023.1

Influence of Halogen Bonding in Catalytic Enantioselective α - Halogenation Reaction

Ishihara, K

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 81 ( 5 ) page： 474 - 482 2023

Chiral π–Cu(II) catalysts for the enantioselective ɑ-amination of N-acyl-3,5-dimethylpyrazoles

Kazuki Nishimura, Yoshihiro Ogura, Kazuki Takeda, Weiwei Guo, and Kazuaki Ishihara

Org. Lett. Vol. 24 ( 41 ) page： 7685 - 7689 2022.10

Multiselective Diels–Alder Reaction of α-Arylacroleins Catalyzed by Boron Tribromide-Assisted Chiral Phosphoric Acids Open Access

Kai Matsui, Kohei Toh, Manabu Hatano, Kazuaki Ishihara

Organic Letters Vol. 24 ( 35 ) page： 6483 - 6488 2022.9

キラルアンモニウム次亜ヨウ素酸塩触媒を用いるエナンチオ選択的酸化的脱芳香族化反応 Invited Reviewed

ウヤヌクムハメット、石原一彰

月刊ファインケミカル【特集】ヨウ素化学の進展と今後の展望 Vol. 51 ( 8 ) page： 31 - 39 2022.8

Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization Open Access

Hiroki Tanaka, Naoya Ukegawa, Muhammet Uyanik, Kazuaki Ishihara

Journal of the American Chemical Society Vol. 144 ( 13 ) page： 5756 - 5761 2022.4

Thorpe–Ingold effect on high-performance chiral –copper(II) catalyst Open Access

Kazuki Nishimura, Kazuaki Ishihara

Synlett Vol. 33 ( 06 ) page： 585 - 588 2022.4

π–Cu(II)–π complex as an extremely active catalyst for enantioselective α-halogenation of N-acyl-3,5-dimethylpyrazoles Open Access

Kazuaki Nishimura, Yanzhao Wang, Yoshihiro Ogura, Jun Kumagai, Kazuaki Ishihara

ACS Catalysis Vol. 12 ( 2 ) page： 1012 - 1017 2022.1

Cp*RhIII/Chiral Disulfonate/CuOAc Catalyst System for the Enantioselective Intramolecular Oxyamination of Alkenes Open Access

Jumpei Hirose, Takumi Wakikawa, Shun Satake, Masahiro Kojima, Manabu Hatano, Kazuaki Ishihara, Tatsuhiko Yoshino, Shigeki Matsunaga

ACS Catalysis Vol. 11 ( 24 ) page： 15187 - 15193 2021.12

Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes Open Access

Muhammet Uyanik, Dai Nagata, Kazuaki Ishihara

Chemical Communications Vol. 57 ( 88 ) page： 11625 - 11628 2021.11

Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry

We report the hypoiodite-catalyzed oxidative C-C homocoupling of arenols to biarenols or biquinones using aqueous hydrogen peroxide as an oxidant. In addition, by combining hypoiodite catalysis and lipophilic Lewis acid-assisted Brønsted acid catalysis under aqueous conditions, we achieved a tandem oxidation/cross-coupling reaction of hydroquinones with electron-rich arenes. These results highlight the substantial scope of hypoiodite/acid co-catalysis for use in oxidative coupling reactions.

DOI： 10.1039/d1cc05171g

Oxidative Ritter-type Chloroamidation of Alkenes Using NaCl and Oxone Open Access

Takehiro Kato, Yuya Okada, Yuto Fujii, Muhammet Uyanik, Kazuaki Ishihara

Asian Journal of Organic Chemistry Vol. 10 ( 11 ) page： 2907 - 2910 2021.11

Language：English Publishing type：Research paper (scientific journal) Publisher：John Wiley and Sons Inc

We report a practical and environmentally benign method for the oxidative Ritter-type chloroamidation of alkenes using sodium chloride and oxone as a chlorinating source and an oxidant, respectively, in acetonitrile under mild conditions. The reaction proceeded smoothly under non-aqueous conditions without the use of any catalyst. Excellent chemoselectivity (i. e., chloroamidation versus dichlorination) could be achieved for electron-deficient styrenes. In addition, this protocol could be easily applied to 7-gram-scale synthesis.

DOI： 10.1002/ajoc.202100575

Open Access

Web of Science

Scopus

Radical Cation [4+2] Cycloaddition of Non-Conjugated Tetrasubstituted Alkenes by an FeCl3/AgSbF6 Co-Initiator Open Access

Shuhei Ohmura, Ryosuke Isogai, Kazuaki Ishihara

Asian Journal of Organic Chemistry Vol. 10 ( 10 ) page： 2534 - 2537 2021.10

Language：English Publishing type：Research paper (scientific journal) Publisher：John Wiley and Sons Inc

Radical cation [4+2] cycloaddition is an alternative strategy for constructing various six-membered rings that cannot be easily accessed by thermal [4+2] cycloaddition. Here, we developed an FeCl3/AgSbF6 co-initiator to promote radical cation [4+2] cycloaddition of non-conjugated tetrasubstituted alkenes with 2,3-dimethyl-1,3-butadiene. In the presence of 10 mol% of FeCl3 and 30 mol% of AgSbF6, the reaction proceeded smoothly in MeCN to provide the cycloadducts from tetrasubstituted alkenes having an electron-rich aromatic group, which improved the yield. We demonstrate the efficiency of an FeCl3/AgSbF6 co-initiator by comparing our finding to the results with previously reported iron(III) initiators in an investigation of the substrate scope. In addition, a kinetic study was conducted to elucidate the detailed reaction mechanism, in which the rate-determining step can be facilitated by intramolecular single electron transfer.

DOI： 10.1002/ajoc.202100473

Open Access

Web of Science

Scopus

触媒的ペプチド合成の最前線 Invited Reviewed

石原一彰

ファルマシア Vol. 57 ( 9 ) page： 804 - 809 2021.9

光学活性ビナフチルジスルホン酸(BINSA)を用いる精密分子触媒設計と不斉合成 Invited Reviewed

石原一彰

硫酸と工業 Vol. 74 ( 6 ) page： 71 - 85 2021.6

Enantio- And Diastereoselective Carbonyl-Ene Cyclization-Acetalization Tandem Reaction Catalyzed by Tris(pentafluorophenyl)borane-Assisted Chiral Phosphoric Acids Open Access

Hideyuki Ishihara, Jianhao Huang, Takuya Mochizuki, Manabu Hatano, Kazuaki Ishihara

ACS Catalysis Vol. 11 ( 10 ) page： 6121 - 6127 2021.5

Language：English Publishing type：Research paper (scientific journal) Publisher：American Chemical Society

Highly enantio- and diastereoselective carbonyl-ene cyclization was developed with the use of chiral Lewis acid-assisted chiral Brønsted acid (LBA) catalysts, which were prepared in situ from both sterically demanding tris(pentafluorophenyl)borane and chiral phosphoric acids. Along with the performance of standard carbonyl-ene cyclizations, carbonyl-ene cyclization-acetalization tandem reactions with the use of additional aldehydes were demonstrated with high enantio- and diastereoselectivities. On the basis of mechanistic examinations, a stepwise reaction pathway via tertiary carbocation intermediates involving possible transition states is proposed.

DOI： 10.1021/acscatal.1c01242

Open Access

Web of Science

Scopus

Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives Open Access

Hiroyuki Hayashi, Shotaro Yasukochi, Tatsuhiro Sakamoto, Manabu Hatano, Kazuaki Ishihara

The Journal of Organic Chemistry Vol. 86 ( 7 ) page： 5197 - 5212 2021.4

Synthesis of chiral organoiodine catalyst for enantioselective oxidative dearomatization reactions: N,N'-(2S,2'S)-(2-iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide) Invited Reviewed

Muhammet Uyanik, Shinichi Ishizaki and Kazuaki Ishihara

Org. Synth. Vol. 98 page： 1 - 7 2021.2

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Papers - ISHIHARA Kazuaki