Faculty Profiles - ISHIHARA Kazuaki

Papers - ISHIHARA Kazuaki

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Front Cover: Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone (Eur. J. Org. Chem. 1/2019) Reviewed

Muhammet Uyanik, Naoto Sahara, Kazuaki Ishihara

European Journal of Organic Chemistry Vol. 2019 ( 1 ) page： 1 - 1 2019.1

Author Correction: Pentamethylcyclopentadienyl rhodium(iii)–chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization Reviewed Open Access

Shun Satake, Takumaru Kurihara, Keisuke Nishikawa, Takuya Mochizuki, Manabu Hatano, Kazuaki Ishihara, Tatsuhiko Yoshino, Shigeki Matsunaga

Nature Catalysis Vol. 2 ( 1 ) page： 94 2019.1

[解説] “デザイン型Brønsted酸触媒を用いるエナンチオ選択的アザ-Friedel-Crafts反応” Invited Reviewed

波多野学，石原一彰

触媒 Vol. 61 ( 5 ) page： 298-304 2019

Designer C2-symmetric Chiral Diamide-type Organoiodine Catalysts Invited Reviewed

Muhammet Uyanik and Kazuaki Ishihara

TCIMAIL ( 182 ) page： 2-14 2019

デザイナーC2対称ジアミド型キラルヨードアレーン触媒

ウヤヌクムハメット、石原一彰

TCIメール ( 182 ) page： 2-16 2019

Synthesis of 1,1-Spirobiindane-7,7-Disulfonic Acid and Disulfonimide: Application for Catalytic Asymmetric Aminalization Open Access

Kurihara Takumaru, Satake Shun, Hatano Manabu, Ishihara Kazuaki, Yoshino Tatsuhiko, Matsunaga Shigeki

CHEMISTRY-AN ASIAN JOURNAL Vol. 13 ( 17 ) page： 2378 - 2381 2018.9

Enantioselective aza-Friedel-Crafts reaction of furan with alpha-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts Open Access

Manabu Hatano, Haruka Okamoto, Taro Kawakami, Kohei Toh, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

CHEMICAL SCIENCE Vol. 9 ( 30 ) page： 6361 - 6367 2018.8

Language：English Publishing type：Research paper (scientific journal) Publisher：ROYAL SOC CHEMISTRY

Chiral C-2- and C-1-symmetric BINOL-derived bis(phosphoric acid) catalysts, which have OP(=O)(OH)(2)/OP(=O)(OH)(OR) moieties at the 2,2 0 - positions, were developed and used for the enantioselective azaFriedel-Crafts reaction of 2-methoxyfuran with alpha-ketimino esters for the first time. The intramolecular conjugated double hydrogen bond network is a key to increasing the Bronsted acidity and preventing deactivation of the catalysts. Highly functionalized alpha-amino acid derivatives with a chiral quaternary carbon center could be transformed into versatile optically active N- and O-heterocycles and an a- arylsubstituted serine.

DOI： 10.1039/c8sc02290a

Open Access

Web of Science

PubMed

ホウ素触媒でカルボン酸を自在に変換する！　アシロキシボラン中間体を鍵とするエナンチオ選択的変換反応

堀部貴大、石原一彰

化学 Vol. 73 ( 8 ) page： 25-28 2018.8

Pentamethylcyclopentadienyl rhodium(III)/chiral disulfonate hybrid catalysis for enantioselective C–H bond functionalization

Shun Satake, Takumaru Kurihara, Keisuke Nishikawa, Takuya Mochizuki, Manabu Hatano, Kazuaki Ishihara, Tatsuhiko Yoshino, Shigeki Matsunaga

Nat. Catal. Vol. 1 ( 8 ) page： 585 - 591 2018.8

Thiourea–I2 as Lewis base–Lewis acid cooperative catalysts for iodochlorination of alkene with in situ-generated I–Cl Open Access

Takahiro Horibe, Yasutaka Tsuji, Kazuaki Ishihara

ACS Catal. Vol. 8 ( 7 ) page： 6362 - 6366 2018.7

Preface Invited Open Access

Ishihara Kazuaki

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN Vol. 76 ( 6 ) page： 563-563 2018.6

The: Ortho -substituent on 2,4-bis(trifluoromethyl)phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines Open Access

Ke Wang, Yanhui Lu, Kazuaki Ishihara

Chemical Communications Vol. 54 ( 43 ) page： 5410 - 5413 2018.5

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

2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2:2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation. This catalyst works for α-dipeptide synthesis.

DOI： 10.1039/c8cc02558d

Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids

Yanhui Lu, Hidefumi Nakatsuji, Yukimasa Okumura, Lu Yao, Kazuaki Ishihara

Journal of the American Chemical Society Vol. 140 ( 19 ) page： 6039 - 6043 2018.5

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

Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.

DOI： 10.1021/jacs.8b02607

Web of Science

Scopus

PubMed

Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate Open Access

Manabu Hatano, Yuji Tabata, Yurika Yoshida, Kohei Toh, Kenji Yamashita, Yoshihiro Ogura, Kazuaki Ishihara

Green Chemistry Vol. 20 ( 6 ) page： 1193 - 1198 2018.3

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

Environmentally benign metal-free tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid self-decomposition at ≤110 °C, and are reusable. In particular, chelating substrates, such as amino alcohols, diols, triols, sugar derivatives, alkaloids, α-amino acid esters, etc., which deactivate conventional metal salt catalysts, can be used. A 100 gram scale biodiesel production was also demonstrated.

DOI： 10.1039/c7gc03858e

Open Access

Web of Science

Scopus

ボロン酸触媒を用いるアミド縮合反応 Invited Reviewed

石原一彰

PETROTECH Vol. 41 ( 1 ) page： 16-19 2018.1

Enantioselective Aza-Friedel-Crafts Reaction of Indoles with Ketimines Catalyzed by Chiral Potassium Binaphthyldisulfonates

Manabu Hatano, Takuya Mochizuki, Keisuke Nishikawa, Kazuaki Ishihara

ACS Catalysis Vol. 8 ( 1 ) page： 349 - 353 2018.1

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

The enantioselective aza-Friedel-Crafts reaction of indoles with low-reactive ketimines has been developed in the presence of a chiral monopotassium binaphthyldisulfonate as a strong Brønsted acid catalyst. A broad substrate scope was achieved, and the corresponding 3-indolylmethanamines with a chiral quaternary carbon center were obtained in high yields with high enantioselectivities. The addition of a catalytic amount of acetic acid considerably promoted the reaction, and a gram-scale reaction could be achieved with reduced catalyst loading.

DOI： 10.1021/acscatal.7b03708

Web of Science

Scopus

Synthesis of 1,1’-spirobiindane-7,7’-disulfonic acid and disulfonimide: Application for catalytic asymmetric aminalization Reviewed Open Access

Takumaru Kurihara, Shun Satake, Manabu Hatano, Kazuaki Ishihara, Tatsuhiko Yoshino, Shigeki Matsunaga

Chem. Asian J. Vol. 13 ( 17 ) page： 2373 - 2377 2018

Chiral supramolecular U-shaped catalysts induce the multiselective Diels–Alder reaction of propargyl aldehyde Reviewed

Manabu Hatano, Tatsuhiro Sakamoto, Tomokazu Mizuno, Yuta Goto, Kazuaki Ishihara

J. Am. Chem. Soc. Vol. 2018 2018

Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-Friedel–Crafts reaction of phenols Invited Reviewed Open Access

Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji, Akira Sakakura, Manabu Hatano, Kazuaki Ishihara

Synthesis Vol. 50 2018

Bronsted Acid/Lewis Base Hybrid Complexes

Hatano Manabu, Ishihara Kazuaki

CHIRAL LEWIS ACIDS Vol. 62 page： 91 - 120 2018

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Papers - ISHIHARA Kazuaki