Assoc. Prof. Shimizu

Dr. Yohei Shimizu (Original papers/Review)

Original papers

40.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, in press. (DOI: 10.1021/acs.orglett.3c01645)
39.
Direct α-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis.
Sun, K.; Huang, C.-Y. (Dennis); Sawamura, M.; Shimizu, Y.
Synlett, 2023, in press. (DOI: 10.1055/a-2071-4465)
38.
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)
37.
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)
36.
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)
35.
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)
34.
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)
33.
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)
32.
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)
31.
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)
30.
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)
29.
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)
28.
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)
27.
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)
26.
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. (10.1016/j.chempr.2018.11.022)
25.
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)
24.
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)
23.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)
22.
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)
20.
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)
19.
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)
18.
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)
17.
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)
16.
Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions
Murakami, R.; Iwai, T.; Morita Y.; Yamamoto T.; Nagai H.; Shimizu Y.; Kanai M.
J. Am. Chem. Soc. 2015, 137, 7075–7078. (DOI: 10.1021/jacs.5b04175)
15.
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)
14.
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)
13.
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)
12.
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)
11.
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)
10.
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)
9.
Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses
Kimura, Y.; Ito, S.; Shimizu, Y.; Kanai, M.
Org. Lett. 2013, 15, 4130–4133. (DOI: 10.1021/ol401810b)
8.
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)
7.
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)
6.
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)
5.
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)
4.
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)
3.
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)
2.
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)
1.
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
9.
Boron-Catalyzed α-Functionalizations of Carboxylic Acids
Shimizu, Y.; Kanai, M.
Chem. Rec., in press. (DOI: 10.1002/tcr.202200273)
8.
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)
6.
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)
5.
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. 
4.
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)
3.
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)
2.
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)
1.
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)