美多

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美多
チーフ(Mixラボ)
研究分野
有機合成化学、有機金属化学、創薬化学、計算科学
関連ウェブサイト
連絡先

tmita atmark icredd.hokudai.ac.jp

研究紹介

研究テーマ

有機合成化学(新反応開発、触媒設計)

キーワード

新反応開発、二酸化炭素固定化反応、アミノ酸
経歴

経歴(Curriculum Vitae)参照願います。

研究概要

我々の研究グループでは、量子化学計算(Gaussian, およびGRRM (AFIRを搭載))を基盤とした新しい分子変換反応の開発を通して、高付加価値化合物(例:フルオロアミノ酸)の化学合成を行っています。触媒反応のみならず様々な反応形式に対応するべく、幅広い有機化学の知識を有する研究者が集まっています。

イオン反応 高反応性のカルベン、ナイトレン、ベンザイン、カルボカチオンなどを基盤とした反応開発を行っています。加えて、豊富で安価、かつ低毒性な一炭素資源である二酸化炭素の固定化反応の開発にも取り組んでいます。

ラジカル反応 ラジカル種の新たな反応性を量子化学計算によって予測して新反応開発に繋げます。ラジカル種を発生させるための紫外光から赤色までの各種LED光源、各種光触媒、電解反応装置、加えて、ラジカルを制御するためのフローシステムの導入も行いました。現在エチレンのラジカル二官能基化反応に焦点を当てて研究を行っています。

ペリ環状反応 原子効率100%で計算化学の予測に最適な反応形式です。Woodward-Hoffmann則に沿った計算予測が可能なため、新しい反応形式、選択性を有する新反応が見つかる可能性があり、その開発に向けて研究を進めています。

遷移金属触媒反応 C-H結合やC-C結合など、遷移金属触媒を用いないと切断しにくい結合を官能基化するための新反応開発を行っています。そのための触媒設計などにも力を入れています。また別途、二酸化炭素の触媒的な固定化にも取り組んでいます。

代表的な研究成果

  • Kanna, W.; Harabuchi, Y.; Takano, H.; Hayashi, H.; Maeda, S.*; Mita, T.* “Carboxylation of a Palladacycle Formed via C(sp3)-H Activation: Theory-Driven Reaction Design” Chem. Asian J. in press.
    DOI: 10.1002/asia.202100989
  • 美多 剛, 前田 理, 髙野 秀明 “エチレンを原料に用いた1,2-ビス(ジフェニルホスフィノ)エタン(DPPE)誘導体の合成法” 特願2021-131481, 2021年8月11日出願.
  • Hayashi, H.; Takano, H.; Katsuyama, H.; Harabuchi, Y.; Maeda, S.*; Mita, T.* “Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO2: Computational Design, Scope, and Application” Chem. Eur. J. 2021, 27 (39), 10040-10047.
    DOI: 10.1002/chem.202100812
  • Mita, T.*; Harabuchi, Y.; Maeda, S.* “Discovery of a Synthesis Method for a Difluoroglycine Derivative Based on a Path Generated by Quantum Chemical Calculations” Chem. Sci. 202011 (29), 7569-7577.
    DOI: 10.1039/D0SC02089C
  • Mita, T.*; Uchiyama, M.; Sato, Y.* “Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)-H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds” Adv. Synth. Catal. 2020, 362 (6), 1275-1280.
    DOI: 10.1002/adsc.201901533
  • Mita, T.*; Ishii, S.; Higuchi, Y.; Sato, Y.* “Pd-Catalyzed Dearomative Carboxylation of Indolylmethanol Derivatives” Org. Lett. 2018, 20 (23), 7603-7606.
    DOI: 10.1021/acs.orglett.8b03337
  • Michigami, K.; Mita, T.*; Sato, Y.* “Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO2J. Am. Chem. Soc. 2017, 139 (17), 6094-6097.
    DOI: 10.1021/jacs.7b02775
  • Mita, T.*; Sugawara, M.; Sato, Y.* “One-Pot Synthesis of α-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration” J. Org. Chem. 2016, 81 (12), 5236-5243.
    DOI: 10.1021/acs.joc.6b00837
  • Mita, T.*; Higuchi, Y.; Sato, Y.* “Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO2 Chem. Eur. J. 2015, 21 (46), 16391-16394.
    DOI: 10.1002/chem.201503359
  • Mita, T.*; Sugawara, M.; Saito, K.; Sato, Y.* “Catalytic Enantioselective Silylation of N-Sulfonylimines: Asymmetric Synthesis of α-Amino Acids from CO2 via Stereospecific Carboxylation of α-Amino Silanes” Org. Lett. 2014, 16 (11), 3028-3031.
    DOI: 10.1021/ol501143c
  • Mita, T.*; Ikeda, Y.; Michigami, K.; Sato, Y.* “Iridium-Catalyzed Triple C(sp3)-H Borylations: Construction of Triborylated Sp3-Carbon Centers” Chem. Commun. 2013, 49 (49), 5601-5603.
    DOI: 10.1039/C3CC42675K
  • Mita, T.*; Chen, J.; Sugawara, M.; Sato, Y.* “One-Pot Synthesis of α-Amino Acids from Imines through CO2Incorporation: An Alternative Method for Strecker Synthesis” Angew. Chem. Int. Ed. 2011, 50 (6), 1393-1396.
    DOI: 10.1002/anie.201006422

関連する研究記事

業績一覧

2021年

  • Synthesis of Difluoroglycine Derivatives from Amines, Difluorocarbene, and CO2: Computational Design, Scope, and Applications
    H. Hayashi, H. Takano, H. Katsuyama, Y. Harabuchi, S. Maeda, T. Mita, Chem. Eur. J., 2021, 27, 10040-10047
    DOI: 10.1002/chem.202100812
  • Chemoselective Cleavage of Si-C(sp(3)) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)
    K. Matsuoka, N. Komami, M. Kojima, T. Mita, K. Suzuki, S. Maeda, T. Yoshino, S. Matsunaga, J. Am. Chem. Soc., 2021, 143, 103-108
    DOI: 10.1021/jacs.0c11645

2020年

  • Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)-H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds
    T. Mita, M. Uchiyama, Y. Sato, Adv. Synth. Catal., 2020, 362, 1275-1280
    DOI: 10.1002/adsc.201901533
  • Discovery of a Synthesis Method for a Difluoroglycine Derivative Based on a Path Generated by Quantum Chemical Calculations
    T. Mita, Y. Harabuchi, S. Maeda, Chem. Sci., 2020, 11, 7569-7577
    DOI: 10.1039/d0sc02089c
  • General Synthesis of Trialkyl- and Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis
    R. Shishido, M. Uesugi, R. Takahashi, T. Mita, T. Ishiyama, K. Kubota, H. Ito, J. Am. Chem. Soc., 2020, 142, 14125-14133
    DOI: 10.1021/jacs.0c03011

2019年

  • Catalytic Carboxylation of Heteroaromatic Compounds: Double and Single Carboxylation with CO2
    T. Mita, H. Masutani, S. Ishii, Y. Sato, Synlett, 2019, 30, 841-844
    DOI: 10.1055/s-0037-1612414
  • Syntheses of α-Amino Acids by Using CO2 as a C1 Source
    T. Mita, Y. Sato, Chem. Asian J., 2019, 14, 2038-2047
    DOI: 10.1002/asia.201900379

2018年

  • Pd-Catalyzed Dearomative Carboxylation of Indolylmethanol Derivatives
    T. Mita, S. Ishii, Y. Higuchi, Y. Sato, Org. Lett., 2018, 20, 7603-7606
    DOI: 10.1021/acs.orglett.8b03337
  • Cobalt-Catalyzed Nucleophilic Addition of the Allylic C(sp3)-H Bond of Simple Alkenes to Ketones
    T. Mita, M. Uchiyama, K. Michigami, Y. Sato, Beilstein J. Org. Chem., 2018, 14, 2012-2017
    DOI: 10.3762/bjoc.14.176

2017年

  • Palladium-Catalyzed Intramolecular Arylative Carboxylation of Allenes with CO2 for the Construction of 3-Substituted Indole-2-Carboxylic Acids
    Y. Higuchi, T. Mita, Y. Sato, Org. Lett., 2017, 19, 2710-2713
    DOI: 10.1021/acs.orglett.7b01055
  • Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO2
    K. Michigami, T. Mita, Y. Sato, J. Am. Chem. Soc., 2017, 139, 6094-6097
    DOI: 10.1021/jacs.7b02775
  • Cobalt-Catalyzed Direct Addition of Allylic C(sp3)-H Bonds to Ketones
    T. Mita, S. Hanagata, K. Michigami, Y. Sato, Org. Lett., 2017, 19, 5876-5879
    DOI: 10.1021/acs.orglett.7b02871

2016年

  • Stereoretentive Addition of N-Tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines
    T. Mita, K. Saito, M. Sugawara, Y. Sato, Chem. Asian J., 2016, 11, 1528-1531
    DOI: 10.1002/asia.201600270
  • One-Pot Synthesis of α-Amino Acids through Carboxylation of Ammonium Ylides with CO2 Followed by Alkyl Migration
    T. Mita, M. Sugawara, Y. Sato, J. Org. Chem., 2016, 81, 5236-5243
    DOI: 10.1021/acs.joc.6b00837
  • Palladium-Catalyzed Carboxylation of Activated Vinylcyclopropanes with CO2
    T. Mita, H. Tanaka, Y. Higuchi, Y. Sato, Org. Lett., 2016, 18, 2754-2757
    DOI: 10.1021/acs.orglett.6b01231

2015年

  • Development of Catalytic C(sp3)-H Silylation and Triborylation Followed by Carboxylation with CO2
    T. Mita, Yuki Gosei Kagaku Kyokaishi, 2015, 73, 810-820
    DOI: 10.5059/yukigoseikyokaishi.73.810
  • Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO2
    T. Mita, Y. Higuchi, Y. Sato, Chem. Eur. J., 2015, 21, 16391-16394
    DOI: 10.1002/chem.201503359
  • A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions
    T. Mita, K. Suga, K. Sato, Y. Sato, Org. Lett., 2015, 17, 5276-5279
    DOI: 10.1021/acs.orglett.5b02645

2014年

  • Synthesis of Arylglycines from CO2 through α-Amino Organomanganese Species
    T. Mita, J. Chen, Y. Sato, Org. Lett., 2014, 16, 2200-2203
    DOI: 10.1021/ol500701n
  • Carboxylation with CO2 via Brook Rearrangement: Preparation of α-Hydroxy Acid Derivatives
    T. Mita, Y. Higuchi, Y. Sato, Org. Lett., 2014, 16, 14-17
    DOI: 10.1021/ol403099f
  • Catalytic Enantioselective Silylation of N-Sulfonylimines: Asymmetric Synthesis of α-Amino Acids from CO2 via Stereospecific Carboxylation of α-Amino Silanes
    T. Mita, M. Sugawara, K. Saito, Y. Sato, Org. Lett., 2014, 16, 3028-3031
    DOI: 10.1021/ol501143c
  • Ruthenium-Catalyzed C-H Silylation of 1-Arylpyrazole Derivatives and Fluoride-Mediated Carboxylation: Use of Two Nitrogen Atoms of the Pyrazole Group
    T. Mita, H. Tanaka, K. Michigami, Y. Sato, Synlett, 2014, 25, 1291-1294, 4 pp.
    DOI: 10.1055/s-0033-1341230

2013年

  • One-Step Synthesis of Racemic α-Amino Acids from Aldehydes, Amine Components, and Gaseous CO2 by the Aid of a Bismetal Reagent
    T. Mita, Y. Higuchi, Y. Sato, Chem. Eur. J., 2013, 19, 1123-1128
    DOI: 10.1002/chem.201202332
  • Iridium-Catalyzed Triple C(sp3)-H Borylations: Construction of Triborylated sp3-Carbon Centers
    T. Mita, Y. Ikeda, K. Michigami, Y. Sato, Chem. Commun., 2013, 49, 5601-5603
    DOI: 10.1039/c3cc42675k
  • Iridium- and Rhodium-Catalyzed Dehydrogenative Silylations of C(sp3)-H Bonds Adjacent to a Nitrogen Atom Using Hydrosilanes
    T. Mita, K. Michigami, Y. Sato, Chem. Asian J., 2013, 8, 2970-2973
    DOI: 10.1002/asia.201300930
  • One-Pot Synthesis of α-Amino Acids from CO2 Using Bismetal Reagents
    T. Mita, Y. Sato, Yuki Gosei Kagaku Kyokaishi, 2013, 71, 1163-1171
    DOI: 10.5059/yukigoseikyokaishi.71.1163

2012年

  • One-Pot Synthesis of α-Amino Acids from CO2 Using a Bismetal Reagent with Si-B Bond
    T. Mita, J. Chen, M. Sugawara, Y. Sato, Org. Lett., 2012, 14, 6202-6205
    DOI: 10.1021/ol302952r
  • Convenient and Practical Synthesis of α-Amido Stannanes
    T. Mita, Y. Higuchi, Y. Sato, Synthesis, 2012, 44, 194-200
    DOI: 10.1055/s-0031-1289597
  • Sequential Protocol for C(sp3)-H Carboxylation with CO2: Transition-Metal-Catalyzed Benzylic C-H Silylation and Fluoride-Mediated Carboxylation
    T. Mita, K. Michigami, Y. Sato, Org. Lett., 2012, 14, 3462-3465
    DOI: 10.1021/ol301431d
  • Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations of α-Amido and α-Acetoxy Stannanes with Carbon Dioxide
    T. Mita, M. Sugawara, H. Hasegawa, Y. Sato, J. Org. Chem., 2012, 77, 2159-2168
    DOI: 10.1021/jo202597p

2011年

  • One-Pot Synthesis of α-Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis
    T. Mita, J. Chen, M. Sugawara, Y. Sato, Angew. Chem., Int. Ed., 2011, 50, 1393-1396
    DOI: 10.1002/anie.201006422
  • Practical Synthesis of N-Boc- and N-Cbz-α-Amido Stannanes from α-Amido Sulfones Using TMSSnBu3 and CsF
    T. Mita, Y. Higuchi, Y. Sato, Org. Lett., 2011, 13, 2354-2357
    DOI: 10.1021/ol200599d

2009年

  • Bifunctional Asymmetric Catalysis with Hydrogen Chloride: Enantioselective Ring Opening of Aziridines Catalyzed by a Phosphinothiourea
    T. Mita, E. N. Jacobsen, Synlett, 2009, , 1680-1684
    DOI: 10.1055/s-0029-1217344

2007年

  • Toward a Rational Design of the Assembly Structure of Polymetallic Asymmetric Catalysts: Design, Synthesis, and Evaluation of New Chiral Ligands for Catalytic Asymmetric Cyanation Reactions
    I. Fujimori, T. Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M. Kanai, M. Shibasaki, Tetrahedron, 2007, 63, 5820-5831
    DOI: 10.1016/j.tet.2007.02.081
  • Second Generation Catalytic Asymmetric Synthesis of Tamiflu: Allylic Substitution Route
    T. Mita, N. Fukuda, F. X. Roca, M. Kanai, M. Shibasaki, Org. Lett., 2007, 9, 259-262
    DOI: 10.1021/ol062663c

2006年

  • Key Role of the Lewis Base Position in Asymmetric Bifunctional Catalysis: Design and Evaluation of a New Ligand for Chiral Polymetallic Catalysts
    I. Fujimori, T. Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2006, 128, 16438-16439
    DOI: 10.1021/ja067003h
  • De Novo Synthesis of Tamiflu via a Catalytic Asymmetric Ring-Opening of meso-Aziridines with TMSN3
    Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2006, 128, 6312-6313
    DOI: 10.1021/ja061696k
  • Assembly State of Catalytic Modules as Chiral Switches in Asymmetric Strecker Amino Acid Synthesis
    N. Kato, T. Mita, M. Kanai, B. Therrien, M. Kawano, K. Yamaguchi, H. Danjo, Y. Sei, A. Sato, S. Furusho, M. Shibasaki, J. Am. Chem. Soc., 2006, 128, 6768-6769
    DOI: 10.1021/ja060841r

2005年

  • Catalytic Enantioselective Reactions by the Chiral Cobalt Complexes as Lewis Acid Catalysts
    T. Kezuka, T. Mita, I. Iwakura, T. Ikeno, T. Yamada, Yuki Gosei Kagaku Kyokaishi, 2005, 63, 604-615
    DOI: 10.5059/yukigoseikyokaishi.63.604
  • Catalytic Enantioselective Desymmetrization of meso-N-Acylaziridines with TMSCN
    T. Mita, I. Fujimori, R. Wada, J. Wen, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2005, 127, 11252-11253
    DOI: 10.1021/ja053486y
  • Catalytic Enantioselective Conjugate Addition of Cyanide to α,β-Unsaturated N-Acylpyrroles
    T. Mita, K. Sasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2005, 127, 514-515
    DOI: 10.1021/ja043424s

2003年

  • Enantioselective 1,3-Dipolar Cycloaddition Reaction of Nitrones with α,β-Unsaturated Aldehydes Catalyzed by Cationic 3-Oxobutylideneaminatocobalt(III) Complexes
    S. Kezuka, N. Ohtsuki, T. Mita, Y. Kogami, T. Ashizawa, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn., 2003, 76, 2197-2207
    DOI: 10.1246/bcsj.76.2197
  • Enantioselective 1,3-Dipolar Cycloaddition Reactions between Nitrones and α-Substituted α,β-Unsaturated Aldehydes Catalyzed by Chiral Cationic Cobalt(III) Complexes
    N. Ohtsuki, S. Kezuka, Y. Kogami, T. Mita, T. Ashizawa, T. Ikeno, T. Yamada, Synthesis, 2003, , 1462-1466
    DOI:

2002年

  • Enantioselective 1,3-Dipolar Cycloaddition of Nitrones Catalyzed by Optically Active Cationic Cobalt(III) Complexes
    T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Org. Lett., 2002, 4, 2457-2460
    DOI: 10.1021/ol026079p

2001年

  • Highly Active 3-Oxobutylideneaminatocobalt Complex Catalysts for an Enantioselective Hetero Diels-Alder Reaction
    S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn., 2001, 74, 1333-1342
    DOI: 10.1246/bcsj.74.1333

2000年

  • Optically Active Cationic Cobalt(III) Complexes: Highly Efficient Catalysts for Enantioselective Hetero Diels-Alder Reaction
    S. Kezuka, T. Mita, N. Ohtsuki, T. Ikeno, T. Yamada, Chem. Lett., 2000, , 824-825
    DOI: 10.1246/cl.2000.824
  • Optically Active Aldiminato Cobalt(II) Complex Catalyst for Enantioselective Hetero-Diels-Alder Reaction
    T. Yamada, S. Kezuka, T. Mita, T. Ikeno, Heterocycles, 2000, 52, 1041-1045
    DOI: 10.3987/COM-99-S126