Faculty Profiles - ISHIHARA Kazuaki

Papers - ISHIHARA Kazuaki

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Chemoselective Oxidative Spiroetherification and Spiroamination of Arenols Using I+/Oxone Catalysis

Muhammet Uyanik, Naoto Sahara, Outa Katade, Kazuaki Ishihara

Organic Letters Vol. 22 ( 2 ) page： 560 - 564 2020.1

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

We developed a chemoselective oxidative dearomative spiroetherification and spiroamination of arenols using I+/oxone catalysis. The intramolecular dearomative C-O and C-N couplings proceeded much more efficiently under slightly acidic conditions to give the corresponding spiro adducts in higher yields compared with previous methods using transition metal or hypervalent iodine catalysts. Control experiments suggested that both hypoiodous acid and iodine might be active species for these reactions.

DOI： 10.1021/acs.orglett.9b04324

Web of Science

Scopus

PubMed

Initiators for radical cation-induced [2 + 2]- and [4 + 2]-cycloadditions of electron-rich Alkenes Open Access

Takahiro Horibe, Kazuaki Ishihara

Chemistry Letters Vol. 49 ( 1 ) page： 107 - 113 2020.1

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

The radical cation-induced [2 + 2]- and [4 + 2]-cycloadditions of electron-rich alkenes afford cyclobutanes and cyclohexenes, which are used in the synthesis of natural products. The key intermediate is the alkene radical cation, which is generated from alkene by a one-electron oxidant. These cycloadditions have attracted renewed attention thanks to the recent development of initiators, such as a chemical oxidant, an electrochemical method and photoredox catalysts. This Highlight Review summarizes these initiators for [2 + 2]- and [4 + 2]-cycloadditions that leverage the generation of the alkene radical cation.

DOI： 10.1246/cl.190790

Web of Science

Scopus

An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide-iron(ii) complexes Open Access

Takahiro Horibe, Keita Nakagawa, Takashi Hazeyama, Kazuki Takeda, Kazuaki Ishihara

Chemical Communications Vol. 55 ( 91 ) page： 13677 - 13680 2019.11

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

An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(ii)-diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2 : 1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS suggest that a 2 : 1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is a pre-catalyst for a Fe(iii)/Fe(iv) redox cycle.

DOI： 10.1039/c9cc07834g

High-performance ammonium hypoiodite/Oxone catalysis for enantioselective oxidative dearomatization of arenols Reviewed

Muhammet Uyanik, Takehiro Kato, Naoto Sahara, Outa Katade, Kazuaki Ishihara

ACS Catal. Vol. 9 ( 12 ) page： 11619-11626 2019.11

ホウ素Lewis酸—キラルリン酸複合触媒を用いるマルチ選択的[2+2]/[4+2]付加環化反応 Invited Reviewed

波多野学，石原一彰

化学工業 Vol. 70 ( 9 ) page： 634-642 2019.9

Highly Active Chiral Dilithium(I) Binaphthyldisulfonate Catalysts for Enantio- and Chemoselective Strecker-Type Reactions

Manabu Hatano, Kosuke Nishio, Takuya Mochizuki, Keisuke Nishikawa, Kazuaki Ishihara

ACS Catalysis Vol. 9 ( 9 ) page： 8178 - 8186 2019.9

Highly active chiral dilithium(I) binaphthyldisulfonate catalysts for enantio- and chemoselective Strecker-type reactions

Manabu Hatano, Kosuke Nishio, Takuya Mochizuki, Keisuke Nishikawa, Kazuaki Ishihara

ACS Catal. Vol. 9 ( 9 ) page： 8178-8196 2019.7

Tris(pentafluorophenyl)borane‐Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction of α,β‐Substituted Acroleins Open Access

Manabu Hatano, Tatsuhiro Sakamoto, Takuya Mochizuki, Kazuaki Ishihara

Asian Journal of Organic Chemistry Vol. 8 ( 7 ) page： 1061 - 1066 2019.7

Front Cover: Tris(pentafluorophenyl)borane‐Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction of α,β‐Substituted Acroleins (Asian J. Org. Chem. 7/2019)

Manabu Hatano, Tatsuhiro Sakamoto, Takuya Mochizuki, Kazuaki Ishihara

Asian Journal of Organic Chemistry Vol. 8 ( 7 ) page： 918 - 918 2019.7