Researcher Profiles - MICHIGAMI Kenichi

写真a

MICHIGAMI Kenichi

Organization

Graduate School of Science Department of Chemistry Assistant Professor
School of Science Department of Chemistry

Affiliation

Institute of Science

Contact information

Affiliation campus

Nakamozu Campus

Position

Graduate School of Science Department of Chemistry

Assistant Professor 2022.04 - Now
School of Science Department of Chemistry

Assistant Professor 2022.04 - Now

Degree

博士（薬科学）（ Hokkaido University ）

Research Areas

Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry
Nanotechnology/Materials / Synthetic organic chemistry
Nanotechnology/Materials / Synthetic organic chemistry
Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry
Informatics / Computational science
Nanotechnology/Materials / Green sustainable chemistry and environmental chemistry
Life Science / Pharmaceutical chemistry and drug development sciences

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Research Interests

Organofluorine Chemistry
Transition Metal Catalyst
Catalysis
Organic Synthesis
Organic Chemistry
Organocatalyst
Carbon Dioxide
Carboxylic Acid

Research subject summary

新規低原子価遷移金属錯体の創製と触媒的分子変換への応用
新規フッ素化含窒素複素環カルベンの創製とその配位子・触媒機能探索
ホウ素の特性を活用した有機酸類の革新的触媒変換法の開発

Research Career

新規低原子価遷移金属錯体の創製と触媒的分子変換への応用

低原子価遷移金属錯体、電子求引性配位子、過剰還元、安定結合切断、触媒的分子変換 Individual

2019.10 - Now
Development of Fluorinated N-Heterocyclic Carbenes as Ligands and Organocatalysts

N-Heterocyclic Carbene (NHC), Redox Activity, Fluorinated Compounds, Organocatalyst, Ligand Individual

2019.10 - Now
Catalytic Transformations of Organic Acids Based on the Unique Features of Boron Compounds

Boron Compounds, Mixed Anhydrides, Transition Metal Complexes, C-O Bond Cleavage, Catalytic Transformations Individual

2019.04 - Now

Professional Memberships

フッ素化学会

2023.10 - Now
有機合成化学協会

2017.04 - Now Domestic
日本化学会

2012.11 - Now Domestic
日本薬学会

2011.11 - Now Domestic
THE CHEMICAL SOCIETY OF JAPAN
THE PHARMACEUTICAL SOCIETY OF JAPAN
有機合成化学協会

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Awards

Best Oral Presentation Award

2016.10 The 6th Junior International Conference on Cutting-Edge Organic Chemistry in Asia

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Country：Japan

Job Career (off-campus)

Osaka Metropolitan University Graduate School of Science Department of Chemistry

2022.04 - Now
Osaka Prefecture University Department of Chemistry, Graduate School of Science

2019.10 - Now
Kyoto University Graduate School of Pharmaceutical Sciences Specially Appointed Assistant Professor

2018.04 - 2019.09

Papers

Isolation of Cationic η<sup>3</sup>-Allenylnickel(II) Key Intermediate Complexes: Origins of Enantioselectivity and Regioselectivity in Nickel(0)-Catalyzed Asymmetric Propargylic Substitutions Reviewed

Yusuke Miyazaki, Kenichi Michigami, Masato Ohashi

Journal of the American Chemical Society 146 ( 12 ) 8757 - 8767 2024.03（ ISSN:0002-7863 ）（ eISSN:1520-5126 ）

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Authorship：Corresponding author Publishing type：Research paper (scientific journal)

DOI： 10.1021/jacs.4c01738

PubMed
Asymmetric cyclization catalyzed by a chiral phosphoric acid–gold(I) hybrid complex as a multifunctional catalyst Reviewed

Naoya Taniguchi, Mitsuhiro Ueda, Kenichi Michigami, Seiji Mori, Masato Ohashi

Bulletin of the Chemical Society of Japan 97 ( 3 ) 2024.02（ ISSN:0009-2673 ）（ eISSN:1348-0634 ）

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Publishing type：Research paper (scientific journal)

Abstract

We herein report the development of a novel hybrid complex containing gold(I) and a chiral phosphoric acid moiety to generate a multifunctional catalyst. While the use of chiral phosphoric acid as a bifunctional catalyst is a common strategy in asymmetric organic synthesis, chiral phosphoric acid–transition metal hybrid complexes as multifunctional catalysts have not been investigated. Thus, we designed and synthesized a novel gold(I) hybrid complex as a multifunctional catalyst that promotes asymmetric catalytic reactions through multipoint nonclassical noncovalent interactions in substrates that lack classical hydrogen-bond donors. In addition, we demonstrate its usefulness as a multifunctional catalyst by successfully developing the first catalytic asymmetric synthesis of dihydrocyclohepta[b]indoles. Experimental and theoretical studies revealed that this asymmetric catalytic reaction involves the kinetic resolution of the reaction intermediate, and that the favored diastereomeric transition state for yielding enantiomeric products is formed through multipoint nonclassical noncovalent interactions originating from the acid–base nature of the chiral phosphoric acid moiety.

DOI： 10.1093/bulcsj/uoae026

Other URL： https://academic.oup.com/bcsj/article-pdf/97/3/uoae026/57095987/uoae026.pdf
Merging Pd(0)-Catalyzed Selective C<inf>acyl</inf>-O Bond Activation of Enol Esters with π-Acid Catalysis: Net Hydroxyacylation of Aliphatic Alkynes with Carboxylic Acids

Michigami K.

ACS Catalysis 12647 - 12653 2024

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DOI： 10.1021/acscatal.4c03945
Novel aza-Michael addition-asymmetric protonation to α,β-unsaturated carboxylic acids with chiral thiourea-boronic acid hybrid catalyst Reviewed

Hiroki Murakami, Ayano Yamada, Kenichi Michigami, *Yoshiji Takemoto

Asian Journal of Organic Chemistry 10 ( 5 ) 1097 - 1101 2021.03

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Publishing type：Research paper (scientific journal) International / domestic magazine：International journal

DOI： 10.1002/ajoc.202100145
Catalytic dehydrative peptide synthesis with gem-diboronic acids Reviewed

Kenichi Michigami, Tatsuhiko Sakaguchi, Yoshiji Takemoto

ACS Catalysis 10 ( 1 ) 683 - 688 2020.01（ ISSN:2155-5435 ）（ eISSN:2155-5435 ）

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Authorship：Lead author Publishing type：Research paper (scientific journal) International / domestic magazine：International journal

Copyright © 2019 American Chemical Society. Alkane-gem-diboronic acids have emerged as versatile organoboron catalysts for dehydrative amidation of α-Amino acids. A phenol-substituted multiboron catalyst with a B-C-B structure outperformed simple arylboronic acids in the condensation of α-Amino acids with suppressed epimerization of electrophiles. gem-diboronic acid catalysis were compatible with various O, N, and S-functionalized α-Amino acids bearing N-protecting groups including common carbamates used in peptide synthesis (Boc, Cbz, Fmoc). N-Trifluoroacetyl protection enabled an unprecedented catalytic dehydrative peptide synthesis at room temperature. Preliminary mechanistic studies revealed carboxylate-binding nature of gem-diboronic acids, orthogonal to the activation of carboxylic acids by arylboronic acids. The distinctive reactivity of the gem-diboronic acids would open prospects for mild catalytic peptide condensation.

DOI： 10.1021/acscatal.9b03894
Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea/boronic acids. Reviewed

Kenichi Michigami, Hiroki Murakami, Takeru Nakamura, Noboru Hayama, Yoshiji Takemoto

Organic & biomolecular chemistry 17 ( 9 ) 2331 - 2335 2019.02（ ISSN:1477-0539 ）

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Authorship：Lead author Publishing type：Research paper (scientific journal) International / domestic magazine：International journal

The first chemical enantioselective synthesis of N-hydroxyaspartic acid derivatives using chiral multifunctional thiourea/boronic acid organocatalysts was developed. A series of fumaric monoacids underwent an intermolecular asymmetric aza-Michael addition of O-alkyl hydroxylamines in excellent regioselectivity. The addition of another carboxylic acid raised the enantiomeric enrichment up to 97% ee. O-Deprotection of the aza-Michael adduct provided an aspartate-derived hydroxylamine fragment applicable for KAHA (α-keto acid-hydroxylamine) ligation.

DOI： 10.1039/c9ob00045c

PubMed
Cobalt-catalyzed nucleophilic addition of the allylic C(sp³)–H bond of simple alkenes to ketones Reviewed

Tsuyoshi Mita*, Masashi Uchiyama, Kenichi Michigami and Yoshihiro Sato*

Beilstein Journal of Organic Chemistry 雑誌 14 2012 - 2017 2018.08

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.3762/bjoc.14.176
Co-Catalyzed Direct Addition of Allylic C(sp³)-H Bonds to Ketones Reviewed

Tsuyoshi Mita*, Satoshi Hanagata, Kenichi Michigami and Yoshihiro Sato*

Organic Letters 雑誌アメリカ化学会 19 ( 21 ) 5876 - 5879 2017.10

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1021/acs.orglett.7b02871
Cobalt-Catalyzed Allylic C(sp³)-H Carboxylation with CO₂ Reviewed

Kenichi Michigami, Tsuyoshi Mita* and Yoshihiro Sato*

Journal of American Chemical Society 雑誌アメリカ化学会 139 ( 17 ) 6094 - 6097 2017.04

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Authorship：Lead author Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1021/jacs.7b02775
Hydroxyl-Assisted trans-Reduction of 1,3-Enynes: Application to the Formal Synthesis of (+)-Aspicilin Reviewed International coauthorship

Sebastian Schaubach, Kenichi Michigami, Alois Fürstner*

Synthesis 雑誌 49 ( 01 ) 202 - 208 2016.07

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1055/s-0035-1562381
Ruthenium-Catalyzed C-H Silylation of 1-Arylpyrazole Derivatives and Fluoride-Mediated Carboxylation: Use of Two Nitrogen Atoms of the Pyrazole Group Reviewed

Tsuyoshi Mita*, Hiroyuki Tanaka, Kenichi Michigami, Yoshihiro Sato*

Synlett 雑誌 25 ( 09 ) 1291 - 1294 2014.04

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1055/s-0033-1341230
Iridium- and Rhodium-Catalyzed Dehydrogenative Silylations of C(sp³)-H Bonds Adjacent to a Nitrogen Atom Using Hydrosilanes Reviewed

Tsuyoshi Mita*, Kenichi Michigami, and Yoshihiro Sato*

Chemistry An Asian Journal 雑誌 8 ( 12 ) 2970 - 2973 2013.09

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1002/asia.201300930
Iridium-catalyzed triple C(sp³)-H borylations: construction of triborylated sp³-carbon centers Reviewed

Tsuyoshi Mita*, Yuto Ikeda, Kenichi Michigami and Yoshihiro Sato*

Chemical Communications 雑誌 49 5601 - 5603 2013.05

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Publishing type：Research paper (scientific journal) Kind of work：Joint Work International / domestic magazine：International journal

DOI： 10.1039/C3CC42675K
Sequential protocol for C(sp3)-H carboxylation with CO2: transition-metal-catalyzed benzylic C-H silylation and fluoride-mediated carboxylation. Reviewed

Mita T, Michigami K, Sato Y

Organic letters 14 ( 13 ) 3462 - 5 2012.07（ ISSN:1523-7060 ）

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Publishing type：Research paper (scientific journal) International / domestic magazine：International journal

DOI： 10.1021/ol301431d

PubMed

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Books and Other Publications

末端アルケンを求核剤とするカルボニル化合物の触媒的アリル化反応

道上健一、*美多剛、*佐藤美洋（ Role： Joint author , 総合論文）

有機合成化学協会誌 2022.03 （ ISSN:0037-9980 ）

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Responsible for pages：210-221 Book type：Scholarly book Participation form：First Author
マックス・プランク石炭研究所での留学体験記

道上健一（ Role： Sole author , 海外研究室レポート）

2020.05

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Total pages：28 Responsible for pages：53-54 Book type：Scholarly book
超原子価塩素試薬の簡便合成法とユニークな求電子的アリール化反応 Reviewed

道上健一（ Role： Sole author , Topics 化学系薬学）

ファルマシア 2019.12

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Responsible for pages：1164 Book type：Scholarly book Participation form：Corresponding Author
コバルト触媒でアリル位C(sp3)–H結合を切断し二酸化炭素を組み込む

道上　健一, 美多　剛（ Role： Joint author）

Chem-Station (ケムステ) | 化学ポータルサイト 2017.05

Presentations

N-アルコキシアスパラギン酸誘導体の触媒的不斉合成法の開発

村上弘樹, 中村岳, 道上健一, 小林祐輔, 竹本佳司

日本薬学会年会要旨集 2018.03 (公社)日本薬学会

Charge of on-campus class subject

化学実験1

2024 Weekly class Undergraduate
研究企画ゼミナール

2024 Intensive lecture Graduate school
化学特別演習2A

2024 Intensive lecture Graduate school
化学特別演習1A

2024 Intensive lecture Graduate school
化学特別研究2A

2024 Intensive lecture Graduate school
化学特別研究1A

2024 Intensive lecture Graduate school
化学特別演習4A

2024 Intensive lecture Graduate school
化学特別演習3A

2024 Intensive lecture Graduate school
化学特別研究5A

2024 Intensive lecture Graduate school
化学特別研究4A

2024 Intensive lecture Graduate school
化学特別研究3A

2024 Intensive lecture Graduate school
化学特別演習5A

2024 Intensive lecture Graduate school
基礎化学実験

2024 Weekly class Graduate school
化学実験Ⅱ

2024 Weekly class Undergraduate
化学実験Ⅰ

2024 Weekly class Undergraduate
Laboratory Chemistry

2021 Practical Training
Chemistry Laboratory II

2021 Practical Training
Chemistry Laboratory I

2021 Practical Training Undergraduate

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Social Activities　⇒ Link to the list of Social Activities

薬の正体

Role(s)： Lecturer

Type： Seminar, workshop

大阪公立大学化学セミナー 2022.08

Position

Position

Degree

Degree

Research Areas

Research Areas

Research Interests

Research Interests

Research subject summary

Research subject summary

Research Career

Research Career

Professional Memberships

Professional Memberships

Awards

Awards

Job Career (off-campus)

Job Career (off-campus)

Papers

Papers

Books and Other Publications

Books and Other Publications

Presentations

Presentations

Charge of on-campus class subject

Charge of on-campus class subject

Social Activities ⇒ Link to the list of Social Activities

Social Activities ⇒ Link to the list of Social Activities

Social Activities　⇒ Link to the list of Social Activities

Social Activities　⇒ Link to the list of Social Activities