Faculty Profiles - ISHIHARA Kazuaki

Papers - ISHIHARA Kazuaki

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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 Reviewed 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 Reviewed

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 Reviewed 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 Reviewed 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 Reviewed

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 Reviewed 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 Reviewed

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 Invited Reviewed

Hatano Manabu, Ishihara Kazuaki

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

Application of Detonation Waves to Rocket Engine Chamber

Kasahara, J; Kato, Y; Ishihara, K; Goto, K; Matsuoka, K; Matsuo, A; Funaki, I; Moriai, H; Nakata, D; Higashino, K; Tanatsugu, N

DETONATION CONTROL FOR PROPULSION: PULSE DETONATION AND ROTATING DETONATION ENGINES page： 61 - 76 2018

Selenium-Iodine Cooperative Catalyst for Chlorocyclization of Tryptamine Derivatives Reviewed

Takahiro Horibe, Shuhei Ohmura, Kazuaki Ishihara

ORGANIC LETTERS Vol. 19 ( 20 ) page： 5525 - 5528 2017.10

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Chlorocyclization oftryptamine derivatives has been developed with the use of a - diphenyl diselenide-iodine cooperative catalyst. Various tryptamine derivatives can be smoothly converted to the corresponding C3a-chlorohexahydropyrrolo[233-b]indoles. Additionally, we, demonstrate the formAl total syntheses of (-)-psychotriasine and- (-)-acetylardeernin by introducing nucleophiles to the C3a poSition of the products.

DOI： 10.1021/acs.orglett.7b02613

Web of Science

PubMed

Enantioselective Conjugate Hydrocyanation of alpha,beta-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide Reviewed

Manabu Hatano, Katsuya Yamakawa, Kazuaki Ishihara

ACS CATALYSIS Vol. 7 ( 10 ) page： 6686 - 6690 2017.10

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Enantioselective conjugate hydrocyanation of alpha,beta-unsaturated N-acylpyrroles with the combined use of Me3SiCN, LiCN, and HCN has been developed in the presence of a chiral lithium(I) phosphoryl phenoxide catalyst. This reaction is useful for a variety of N-acylpyrroles, including previously unreported substrates, such as heteroaryl and halogen-substituted N-cinnamoylpyrroles. A gram-scale reaction and subsequent transformations to a (R)-succinate, (S)paraconic acid, and (R)-baclofen demonstrate an entry for the practical synthesis of optically active beta-substituted gamma-amino butyric acids (GABA).

DOI： 10.1021/acscatal.7b02551

Web of Science

Design of Boronic Acid-Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines Reviewed

Yanhui Lu, Ke Wang, Kazuaki Ishihara

ASIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 6 ( 9 ) page： 1191 - 1194 2017.9

Language：English Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

Two novel boronic acid-base complexes were developed as reusable homogeneous catalysts for amide condensation. First, quaternary ammonium resin-bound boronates were shown to be effective catalysts that might release free boronic acids during reactions and could be regenerated afterwards. Next, a 1:1 mixture of 3,5-dinitro-4-tolueneboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) or 4-(N,N,-dimethylamino)pyridine (DMAP) cooperatively promoted amide formation and precipitated as an acid-base solid complex after cooling. These inexpensive and reusable complexes may be useful in large-scale process chemistry.

DOI： 10.1002/ajoc.201700194

Web of Science

Enantioselective cycloaddition of styrenes with aldimines catalyzed by a chiral magnesium potassium binaphthyldisulfonate cluster as a chiral Brønsted acid catalyst Reviewed

Manabu Hatano, Keisuke Nishikawa, Kazuaki Ishihara

Journal of the American Chemical Society Vol. 139 ( 25 ) page： 8424-8427 2017.5

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Papers - ISHIHARA Kazuaki