清水 洋平　Yohei Shimizu

准教授　Associate Professor

清水　洋平　Yohei Shimizu

E-mail: shimizu-y[at]sci.hokudai.ac.jp

略歴

• 1984 長野県に生れる
• 2002 長野県立須坂高校　卒業
• 2006 東京大学薬学部　卒業
• 2008 東京大学大学院薬学系研究科分子薬学専攻修士課程　修了
• 2011 東京大学大学院薬学系研究科分子薬学専攻博士課程　修了
• 2011 東京大学大学院薬学系研究科　助教
• 2012 ケンブリッジ大学化学科　短期留学
• 2018 北海道大学大学院理学研究院化学部門　講師
• 2020 同　准教授

受賞歴

• 2009 第35回反応と合成の進歩シンポジウム　優秀発表賞
• 2013 Frontires in Chemistry, Armenia (ArmChemFront) Best Poster Prize
• 2015 有機合成化学協会「東レ」研究企画賞
• 2018 日本化学会 第98春季年会『第32回若い世代の特別講演会』
• 2019 日本薬学会奨励賞
• 2020 Thieme Chemistry Journals Award 2020
• 2023 2022年度日本化学会北海道支部奨励賞

Original papers

1. Boron-Catalyzed Michael Reaction of Donor-Acceptor Carboxylic Acid Pairs Enabling Direct Synthesis of 1,5-Dicarboxylic Acids.
   Yoshida, Y.; Sawamura, M.; Shimizu, Y. 
   Org. Lett., 2024, 26, 5425–5429. (DOI: 10.1021/acs.orglett.4c01542)
2. Visible-Light-Induced Aminochlorination of Alkenes.
   Mejri, E.; Higashida, K.; Kondo,Y.; Nawachi, A.; Morimoto, H.; Ohshima, T.; Sawamura, M.; Shimizu, Y. 
   Org. Lett. 2023, 25, 4581–4585. (DOI: 10.1021/acs.orglett.3c01645)
3. Direct α-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis.
   Sun, K.; Huang, C.-Y. (Dennis); Sawamura, M.; Shimizu, Y.
   Synlett, 2023, 2210–2214. (DOI: 10.1055/a-2071-4465)
4. Silver-Catalyzed Asymmetric Aldol Reaction of Isocyanoacetic Acid Derivatives Enabled by Cooperative Participation of
   Classical and Nonclassical Hydrogen Bonds.
   Sakai, S.; Fujioka, A.; Imai, K.; Uchiyama, K.; Shimizu, Y.; Higashida, K.; Sawamura, M.
   Adv. Synth. Catal. 2022, 364, 2333-2339. (DOI:10.1002/adsc.202200327)
5. Insights into the Mechanism of Enantioselective Copper-Catalyzed Ring-Opening Allylic Alkylation of Cyclopropanols.
   Kitabayashi, A.; Mizushima, S.; Higashida, K.; Yasuda, Y.; Shimizu, Y.; Sawamura, M. 
   Adv. Synth. Catal. 2022, 364, 1855-1862. (DOI: 10.1002/adsc.202200157)
6. Visible Light-Induced Reductive Alkynylation of Aldehydes by Umpolung Approach.
   Tanaka, I.; Sawamura, M.; Shimizu, Y.
   Org. Lett. 2022, 24, 520–524. (DOI: 10.1021/acs.orglett.1c03927)
7. Synthesis of C,N,N-Cyclometalated Gold(III) Complexes with Anionic Amide Ligands
   Niizeki, R.; Higashida, K.; Mejri, E.; Sawamura, M.; Shimizu, Y.
   Synlett, 2022, 32, 288–292. (DOI: 10.1055/a-1673-9236)
8. Data-Driven Catalyst Optimization for Stereodivergent Asymmetric Synthesis by Iridium/Boron Hybrid Catalysis
   Chen, H.; Yamaguchi, S.; Morita, Y.; Nakao, H.; Zhai, X.-N.; Shimizu, Y.; Mitsunuma, H.; Kanai, M.
   Cell Rep. Phys. Sci. 2021, 2, 100679. (DOI: 10.1016/j.xcrp.2021.100679)
9. Visible-Light-Driven α-Allylation of Carboxylic Acids
   Sun, K. ; Ueno, M. ; Imaeda, K. ; Ueno, K. ; Sawamura, M. ; Shimizu, Y.
   ACS Catal. 2021, 11, 9722–9728. (DOI: 10.1021/acscatal.1c02558)
10. Iridium-Catalyzed Enantioselective Transfer Hydrogenation of Ketones Controlled by Alcohol Hydrogen-Bonding and sp3-C–H Noncovalent Interactions
    Murayama, H.; Heike, Y.; Higashida, K.; Shimizu, Y.; Yodsin, N.; Wongnongwa, Y.; Jungsuttiwong, S.;  Mori, S.; Sawamura, M.
    Adv. Synth. Catal. 2020, 362, 4655–4661. (DOI: 10.1002/adsc.202000615)
11. Copper-Catalyzed Enantioselective Conjugate Reduction of α,β-Unsaturated Esters with Phenol-Carbene Chiral Ligand
    Mimura, S.; Mizushima, S.; Shimizu, Y.; Sawamura, M.
    Beilstein J. Org. Chem. 2020, 16, 537–543. (DOI:10.3762/bjoc.16.50)
12. A Stable and Cleavable O-Linked Spacer for Drug Delivery Systems
    Ito, K.; Tatsumi, T.; Takahashi, K.; Shimizu, Y.; Yamatsugu, K.; Kanai, M.
    Chem. Pharm. Bull. 2020, 68, 212–215. (DOI: 10.1248/cpb.c19-00376)
13. Boron-Catalyzed α-Amination of Carboxylic Acids
    Morisawa, T.; Sawamura, M.; Shimizu, Y.
    Org. Lett. 2019, 21, 7466–7469. (DOI: 10.1021/acs.orglett.9b02769)
14. Copper(I)-Catalyzed Stereodivergent Propargylation of N-Acetyl Mannosamine for Protecting-Group-Minimal Synthesis of C3-Substituted Sialic Acids
    Ishizawa, K.; Majima, S.; Wei, X.-F.; Mitsunuma, H.; Shimizu, Y.; Kanai, M.
    J. Org. Chem. 2019, 84, 10615–10628. (DOI: 10.1021/acs.joc.9b00887)
15. Asymmetric Synthesis of α-Alkylidene-β-Lactams through Copper Catalysis with a Prolinol-Phosphine Chiral Ligand
    Imai, K.; Takayama, H.; Murayama, H., Ohmiya, H.; Shimizu, Y.; Sawamura, M.
    Org. Lett. 2019, 21, 1717–1721. (DOI: 10.1021/acs.orglett.9b00276)
16. Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes to Allenes
    Wei, X.-F.; Wakaki, T.; Itoh, T.; Li, H.-L.; Yoshimura, T.; Miyazaki, A.; Oisaki, K.; Hatanaka, M.; Shimizu, Y.; Kanai, M.
    Chem 2019, 5, 585–599.(DOI: 10.1016/j.chempr.2018.11.022)
17. Copper(I)-Catalyzed Enantio- and Diastereodivergent Borylative Coupling of Styrenes and Imines
    Itoh, T.; Kanzaki, Y.; Shimizu, Y.; Kanai, M.
    Angew. Chem. Int. Ed. 2018, 57, 8265–8269. (DOI: 10.1002/anie.201804117)
18. Chemo- and Enantioselective Pd/B Hybrid Catalysis forthe Construction of Acyclic Quaternary Carbons: Migratory Allylation of O-Allyl Esters to α-C-Allyl Carboxylic Acids
    Fujita, T.; Yamamoto, T.; Morita, Y.; Chen, H.; Shimizu, Y.; Kanai, M.
    J. Am. Chem. Soc. 2018, 140, 5899–5903. (DOI: 10.1021/jacs.8b02783)
19. Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl Ketones
    Ishizawa, K.; Nagai, H.; Shimizu, Y.; Kanai, M.
    Chem. Pharm. Bull. 2018, 66, 231–234. (DOI: 10.1248/cpb.c17-00545)
20. Copper(I)-Catalyzed Enantioselective Addition of Enynes to Ketones
    Wei, X.-F.; Xie, X.-W.; Shimizu, Y.; Kanai, M.
    J. Am. Chem. Soc. 2017, 139, 4647–4650. (DOI: 10.1021/jacs.7b01254)
21. Copper(I)-Catalyzed Dehydrative C-Glycosidation of Unprotected Pyranoses with Ketones
    Wei, X.-F.; Shi, S.-L.; Xie, X.-W.; Shimizu, Y.; Kanai, M.
    ACS Catal. 2016, 6, 6718–6722. (DOI: 10.1021/acscatal.6b02106)
22. Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis of Trialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes
    Itoh, T.; Shimizu, Y.; Kanai, M.
    J. Am. Chem. Soc. 2016, 138, 7528–7531. (DOI: 10.1021/jacs.6b04646)
23. Ligand-Promoted, Boron-Mediated Chemoselective Carboxylic Acid Aldol Reaction
    Nagai, H.; Morita, Y.;Shimizu, Y.; Kanai, M.Org. Lett. 2016, 18, 2076–2079. (DOI: 10.1021/acs.orglett.6b00914)
24. An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed Stereodivergent Propargylation of Unprotected Aldoses
    Wei, X.-F.; Shimizu, Y.; Kanai, M.
    ACS Cent. Sci. 2016, 2, 21–26. (DOI: 10.1021/acscentsci.5b00360)
25. Cu-Catalyzed Oxyboration of Unactivated Alkenes
    Itoh, T.; Matsueda, T.; Shimizu, Y.; Kanai, M.
    Chem. Eur. J. 2015, 21, 15955–15959. (DOI: 10.1002/chem.201503329)
26. Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions
    Morita Y.; Yamamoto T.; Nagai H.; Shimizu Y.; Kanai M.
    J. Am. Chem. Soc. 2015, 137, 7075–7078. (DOI: 10.1021/jacs.5b04175)
27. Structure-based design of a streptavidin mutant specific for an artificial biotin analogue
    Kawato T.; Mizohata E.; Shimizu Y.; Meshizuka T.; Yamamoto T.; Takasu N.; Matsuoka M.; Matsumura H.; Kodama T.; Kanai M.; Doi H.; Inoue T.; Sugiyama A.
    J. Biochem. 2015, 157, 467–475. (DOI: 10.1093/jb/mvv004)
28. Design and synthesis of biotin analogues reversibly binding with streptavidin
    Yamamoto T.; Aoki K.; Sugiyama A.; Doi H.; Kodama T.; Shimizu Y.; Kanai M.
    Chem. Asian. J. 2015, 10, 1071–1078. (DOI: 10.1002/asia.201500120)
29. Structure-based design and synthesis of a bivalent iminobiotin analog showing strong affinity toward a low immunogenic streptavidin mutant
    Kawato T.; Mizohata E.; Shimizu Y.; Meshizuka T.; Yamamoto T.; Takasu N.; Matsuoka M.; Matsumura H.; Kodama T.; Kanai M.; Doi H.; Inoue T.; Sugiyama A.
    Biosci. Biotechnol. Biochem. 2015, 79, 640–642. (DOI: 10.1080/09168451.2014.991692)
30. Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes
    Itoh T.; Shimizu Y.; Kanai M.
    Org. Lett. 2014, 16, 2736–2739. (DOI: 10.1021/ol501022d)
31. Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via consecutive intramolecular amido-cupration of allenes and asymmetric addition of carbonyl compounds 
    Chikkade P. K.; Shimizu Y.; Kanai M.
    Chem. Sci. 2014, 5, 1585–1590. (DOI: 10.1039/C3SC52803K)
32. A Catalytic C-C Bond-Formation with Minimal Use of Protecting Groups: Construction of Functionalized Isotetronic Acid Derivatives
    Shimizu Y.; Yasuda K.; Kanai M.
    HETEROCYCLES 2014, 88, 919–927. (DOI: 10.3987/COM-13-S(S)81)
33. Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses
    Kimura, Y.; Ito, S.; Shimizu, Y.; Kanai, M.
    Org. Lett. 2013, 15, 4130–4133. (DOI: 10.1021/ol401810b)
34. In situ Catalytic Generation of Allylcopper Species for Asymmetric Allylation: Toward 1H-Isochromene Skeletons
    Kawai, J.; Chikkade, P. K.; Shimizu, Y.; Kanai, M.
    Angew. Chem. Int. Ed. 2013, 52, 7177–7180. (DOI: 10.1002/anie.201302027)
35. Copper(I)-Catalyzed Enantioselective Incorporation of Ketones to Cyclic Hemiaminals for the Synthesis of Versatile Alkaloid Precursors
    Shi, S.-L.; Wei, X.-F.; Shimizu, Y.; Kanai, M.
    J. Am. Chem. Soc. 2012, 134, 17019–17022. (DOI: 10.1021/ja308872z)
36. Cu(I)-catalyzed a-alkylation of ketones with styrene derivatives
    Majima, S.; Shimizu, Y.; Kanai, M.
    Tetrahedron Lett. 2012, 53, 4381–4384. (DOI: 10.1016/j.tetlet.2012.06.019)
37. Catalytic Asymmetric Synthesis of R207910
    Saga, Y.; Motoki, R.; Makino, S.; Shimizu, Y.; Kanai, M.; Shibasaki, M.
    J. Am. Chem. Soc. 2010, 132, 7905–7907. (DOI: 10.1021/ja103183r)
38. Asymmetric Reductive Mannich Reaction to Ketoimines Catalyzed by a Cu(I) Complex
    Du, Y.; Xu, L. –W.; Shimizu, Y.; Oisaki, K.; Kanai, M.; Shibasaki, M.
    J. Am. Chem. Soc. 2008, 130, 16146–16147. (DOI: 10.1021/ja8069727)
39. The first catalytic asymmetric total synthesis of ent-hyperforin
    Shimizu, Y.; Shi, S.–L.; Usuda, H.; Kanai, M.; Shibasaki, M.
    Tetrahedron 2010, 66, 6569–6584. (DOI: 10.1016/j.tet.2010.05.086)
40. Catalytic Asymmetric Total Synthesis of ent-Hyperforin
    Shimizu, Y.; Shi, S. –L.; Usuda, H.; Kanai, M.; Shibasaki, M.
    Angew. Chem. Int. Ed. 2010, 49, 1103–1106. (DOI: 10.1002/anie.200906678)
41. New Approach for Construction of a Highly Congested Bicyclic System in Polycyclic Polyprenylated Acylphloroglucinols (PPAPs)
    Shimizu, Y.; Kuramochi, A.; Usuda, H.; Kanai, M.; Shibasaki, M.
    Tetrahedron Lett. 2007, 48, 4173–4177. (DOI: 10.1016/j.tetlet.2007.04.080)

Reviews

1. MHATに基づいた第四級炭素構築反応
   清水洋平
   Organometallic News「有機金属ハイライト」, 2024, 3, 100.
2. Enabling α-Functionalization of Carboxylic Acids by Boron Compounds
   Shimizu, Y.
   J. Synth. Org. Chem. Jpn. 2024, 82, 802-813. (DOI: 10.5059/yukigoseikyokaishi.82.802)
3. The Aldol Reaction: Group XIII Enolates
   Sawamura, M.; Shimizu, Y.
   Comprehenseive Organic Synthesis, 2024, in press. (DOI: 10.1016/B978-0-323-96025-0.00048-X)
4. Synthesis of Carboxylic Acids with Retention of the Functional Group (Update 2024)
   Sawamura, M.; Shimizu, Y.
   Science of Synthesis Knowledge Updates, 2024, 2, 201. (DOI: 10.1055/sos-SD-120-00214)
5. Boron-Catalyzed α-Functionalizations of Carboxylic Acids
   Shimizu, Y.; Kanai, M.
   Chem. Rec. 2023, e202200273. (DOI: 10.1002/tcr.202200273)
6. Boron Catalysis in the Transformation of Carboxylic Acids and Carboxylic Acid Derivatives 
   Sawamura, M.; Shimizu, Y.
   Eur. J. Org. Chem. 2023, 26, e202201249. (DOI: 10.1002/ejoc.202201249)
7. Development of Copper-Catalyzed Chemoselective Reactions
   Shimizu, Y.
   Chem. Pharm. Bull. 2020, 68, 405–420.(DOI: 10.1248/cpb.c19-00739)
8. Cupid and Psyche system for the diagnosis and treatment of advanced cancer
   Sugiyama, A.; Kawamura, T.; Tanaka, T.; Doi, H.; Yamashita, T.; Shinoda, K.; Fujitani, H.; Yamatsugu, K.; Shimizu, Y.; Tatsumi, T.; Takahashi, K.; Kanai, M.; Mizohata, E.; Kawato, T.; Doi, T.; Inoue, T.; Kodama, T.
   Proc. Jpn. Acad., Ser. B 2019, 95, 602–611. (DOI: 10.2183/pjab.95.041)
9. カルボン酸選択的求核的活性化法の開発―単純な試薬の新しい利用法
   清水洋平
   化学と工業（飛翔する若手）2018, 71, 871-872.
10. Catalytic Asymmetric Addition Reactions of Cu(I)-Conjugated Soft Carbon Nucleophiles
    Wei, X.-F.; Shimizu, Y.; Kanai, M.
    Topics in Organometallic Chemistry 2016, 58, 169–182. (DOI: 10.1007/3418_2015_163)
11. Recent progress in copper-catalyzed difunctionalization of unactivated carbon-carbon multiple bonds
    Shimizu, Y.; Kanai, M.
    Tetrahedron Lett. 2014, 55, 3727–3737. (DOI: 10.1016/j.tetlet.2014.05.077)
12. 有機触媒の力　カルボニル‐オレフィンメタセシス
    清水洋平
    ファルマシア 2013, 49, 695. (DOI: 10. 10.14894/faruawpsj.49.7_695)
13. Carbon–Carbon Bond-Formations Promoted by Redox-Active Metal Catalysts
    Kanai, M.; Matsunaga, S.; Oisaki, K.; Shimizu, Y.
    J. Synth. Org. Chem. Jpn. 2013, 71, 433–442. (DOI: 10.5059/yukigoseikyokaishi.71.433)