Curriculum Vitae
Education / Career
2006.3 BS
Department of Pharmaceutical Sciences, The University of Tokyo
Under the supervision of Prof. Masakatsu Shibasaki
2008.3 Master
Graduate School of Pharmaceutical Sciences, The University of Tokyo
Under the supervision of Prof. Masakatsu Shibasaki
2011.3 Ph.D.
Graduate School of Pharmaceutical Sciences, The University of Tokyo
Under the supervision of Prof. Masakatsu Shibasaki (2008.3-2010.3)
Under the supervision of Prof. Motomu Kanai (2010.4-2011.3)
2011.4-2017.12 Assistant Professor
Graduate School of Pharmaceutical Sciences, The University of Tokyo (Prof.
Motomu Kanai)
2012.7-2012.9 Visiting Scientist
Department of Chemistry, University of Cambridge
Under the supervision of Prof. Matthew J. Gaunt
2018.1-present Lecturer
Department of Chemistry, Faculty of Science, Hokkaido University (Prof.
Masaya Sawamura)2019.4-present Lecturer
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD),
Hokkaido University (Prof. Masaya Sawamura)
Membership
Pharmaceutical Society of Japan
Society of Synthetic Organic Chemistry of JapanThe Chemical Society of Japan

Awards
1. Best Poster Prize @ Frontires in Chemistry, Armenia (ArmChemFront 2013)
2. TORAY Award in Synthetic Organic Chemistry, Japan (2015) 「ホウ素触媒と遷移金属触媒の協奏的効果によるカルボン酸の化学選択的修飾反応の開発」
3. 若い世代の特別講演証 (The Chemical Society of Japan Lecture Award)（日本化学会
第 98 春季年会（2018）） 「一価銅触媒の特性を活かした化学選択的反応の開発」
4. 日本薬学会 奨励賞 (the Pharmaceutical Society of Japan Award for YoungScientists) (2019.3.20) 「触媒の特性を活かした化学選択的反応の開発」
5. Thieme Chemistry Journals Award (2020)

Publication
1. Copper-Catalyzed Enantioselective Conjugate Reduction of α,β-Unsaturated Esters
with Phenol-Carbene Chiral Ligand
S. Mimura, S. Mizushima, Y. Shimizu, M. Sawamura*Beilstein J. Org. Chem. 2020, xxx, xx–xx.
2. A Stable and Cleavable O-Linked Spacer for Drug Delivery Systems
K. Ito, T. Tatsumi, K. Takahashi, Y. Shimizu, K. Yamatsugu, M. Kanai*Chem. Pharm. Bull. 2020, 68, 212–215. DOI: 10.1248/cpb.c19-00376

3. Boron-Catalyzed α-Amination of Carboxylic Acids
T. Morisawa, M. Sawamura,* Y. Shimizu*

Org. Lett. 2019, 18, 7466–7469. DOI: 10.1021/acs.orglett.9b02769*Most read articles (1 month) (2019/Sep) of Org. Lett.

4. Copper(I)-Catalyzed Stereodivergent Propargylation of N-Acetyl Mannosamine forProtecting-Group-Minimal Synthesis of C3-Substituted Sialic Acids
K. Ishizawa, S. Majima, X.-F. Wei, H. Mitsunuma, Y. Shimizu,* M. Kanai*

J. Org. Chem. 2019, 84, 10615–10628. DOI: 10.1021/acs.joc.9b00887
OH

OH
H

OH

O

Lewis basic(R)-Cu cat.

O

HO
AcHN

HO

OH

O

OH

OH

NHAc
R

OH

OH

OH

·+NHAc

HO

OH

NHAc

OH

R

D-ManNAc

R

OH

OH

OH

R

Lewis acidic(S)-Cu cat.

Bpin

OH

OH

OH

OH
H

OH

O

OH

HO
AcHN

O
OH

R
OH

Catalyst-dependent stereodivergency
Protecting group-minimal
Three step-synthesis of sialic acid analogues

5. Asymmetric Synthesis of α-Alkylidene-β-Lactams through Copper Catalysis with a
Prolinol-Phosphine Chiral Ligand
K. Imai, Y. Takayama, H. Murayama, H. Ohmiya, Y. Shimizu, M. Sawamura*Org. Lett. 2019, 21, 1717–1721. DOI: 10.1021/acs.orglett.9b00276

6. Catalytic Regio- and Enantioselective Proton Migration from Skipped Enynes toAllenes
X.-F. Wei, T. Wakaki, T. Itoh, H.-L. Li, T. Yoshimura, A. Miyazaki, K. Oisaki, M.
Hatanaka,* Y. Shimizu,* M. Kanai*

Chem 2019, 5, 585–599. DOI: 10.1016/j.chempr.2018.11.022*Featured by Univ. of Tokyo/Hokkaido Univ./ NAIST press release(https://www.hokudai.ac.jp/news/190111_pr.pdf)

7. Chemo- and Enantioselective Pd/B Hybrid Catalysis for the Construction of Acyclic
Quaternary Carbons: Migratory Allylation of O-Allyl Esters to α-C-Allyl Carboxylic
Acids
T. Fujita, T. Yamamoto, Y. Morita, H. Chen, Y. Shimizu,* M. Kanai*

J. Am. Chem. Soc. 2018, 140, 5899-5903. DOI: 10.1021/jacs.8b02783*Most read articles (1 month) (2018/May) of J. Am. Chem. Soc.
8. Copper-Catalyzed Enantio- and Diastereodivergent Borylative Coupling of Styrenes
and Imines
T. Itoh, Y. Kanzaki, Y. Shimizu,* M. Kanai*

Angew. Chem. Int. Ed. 2018, 57, 8265-8269. DOI: 10.1002/anie.201804117*Featured by SYNFACTS: Synfacts 2018, 14, 953. DOI:10.1055/s-0037-1610587
9. Boron-Catalyzed Carboxylic Acid-Selective Aldol Reaction with Trifluoromethyl
Ketones
K. Ishizawa, H. Nagai, Y. Shimizu,* M. Kanai*Chem. Pharm. Bull. 2018, 66, 231-234. DOI: 10.1248/cpb.c17-00545*Selected as one of the cover pictures.

10. Copper(I)-Catalyzed Enantioselective Addition of Enynes to Ketones
X.-F. Wei, X.-W. Xie, Y. Shimizu,* M. Kanai*

J. Am Chem. Soc. 2017, 139, 4647-4650. DOI: 10.1021/jacs.7b01254*Most read articles (1 month) (2017/April) of J. Am. Chem. Soc.
11. Copper(I)-Catalyzed Dehydrative C-Glycosidation of Unprotected Pyranoses withKetones
X.-F. Wei, S.-L. Shi, X.-W. Xie, Y. Shimizu,* M. Kanai*ACS Catalysis 2016, 6, 6718-6722. DOI: 10.1021/acscatal.6b02106

12. Ligand-Enabled, Copper-Catalyzed Regio- and Stereoselective Synthesis ofTrialkylsubstituted Alkenylboronates from Unactivated Internal Alkynes
T. Itoh, Y. Shimizu, M. Kanai*

J. Am Chem. Soc. 2016, 138, 7528-7531. DOI: 10.1021/jacs.6b04646*Featured by Department News
(http://www.f.u-tokyo.ac.jp/news.html?key=1465524032)*Most read articles (1 month) (2016/June) of J. Am. Chem. Soc.
13. Ligand Promoted, Boron Mediated Chemoselective Carboxylic Acid Aldol Reaction
H. Nagai, Y. Morita, Y. Shimizu,* M. Kanai*Org. Lett. 2016, 18, 2276-2279. DOI: 10.1021/acs.orglett.6b00914

*Featured by SYNFACTS: Synfacts 2016, 12, 734. DOI:10.1055/s-0035-1562319
14. An Expeditious Synthesis of Sialic Acid Derivatives by Copper(I)-Catalyzed
Stereodivergent Propargylation of Unprotected Aldoses
X.-F. Wei, Y. Shimizu,* M. Kanai*ACS Cent. Sci. 2016, 2, 21-26. DOI: 10.1021/acscentsci.5b00360*Selected as cover picture.
*Highlighted on ACS Central Science (First Reactions) S. Hong, M. J. Krische ACS

Cent. Sci. 2016, 2, 12-13. DOI:10.1021/acscentsci.6b00002*Most read articles (1 month) (2016/January) of ACS Central Science*Most read articles (12 months) (2016/May-Sep) of ACS Central Science*Featured by Univ. of Tokyo press release(http://www.f.u-tokyo.ac.jp/~kanai/news/wei_press.pdf)
15. Cu-Catalyzed Oxyboration of Unactivated Alkenes
T. Itoh, T. Matsueda, Y. Shimizu,* M. Kanai*Chem. Eur. J. 2015, 21, 15955-15959. DOI:10.1002/chem.201503329*Featured by SYNFACTS: Synfacts 2016, 12, 79. DOI: 10.1055/s-0035-1561019
16. Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids forMannich-Type Reactions
Y. Morita, T. Yamamoto, H. Nagai, Y. Shimizu,* M. Kanai *J. Am. Chem. Soc. 2015, 137, 7075-7078. DOI:10.1021/jacs.5b04175

*Featured by UTokyo Research(http://www.u-tokyo.ac.jp/ja/utokyo-research/research-news/new-carboxylic-acid-sele
ctive-carbon-carbon-bond-forming-reactions.html,
http://www.u-tokyo.ac.jp/en/utokyo-research/research-news/new-carboxylic-acid-sele
ctive-carbon-carbon-bond-forming-reactions.html), Department News
(http://www.f.u-tokyo.ac.jp/news.html?key=1433120385), Chem-Station(http://www.chem-station.com/blog/2015/07/activationcarboxylicacid.html),
SYNFORM: Synform 2015/10, A140–A143. DOI: 10.1055/s-0035-1560166
17. Structure-based design of a streptavidin mutant specific for an artificial biotin
analogue
T. Kawato,a E. Mizohata,a Y. Shimizu,a T. Meshizuka, T. Yamamoto, N. Takasu, M.
Matsuoka, H. Matsumura, T. Kodama, M. Kanai, H. Doi,* T. Inoue,* A. Sugiyama*

J. Biol. Chem. 2015, 6, 467-475. DOI:10.1093/jb/mvv004
aThese authors contributed equally to this work.

18. Structure-based design and synthesis of a bivalent iminobiotin analog showing
strong affinity toward a low immunogenic streptavidin mutant
T. Kawato,a E. Mizohata,a Y. Shimizu,a T. Meshizuka, T. Yamamoto, N. Takasu, M.
Matsuoka, H. Matsumura, T. Kodama, M. Kanai, H. Doi,* T. Inoue,* A. Sugiyama*

Biosci. Biotechnol. Biochem. 2015, 79, 640-642. DOI:10.1080/09168451.2014.991692
aThese authors contributed equally to this work.

19. Design and Synthesis of biotin analogues reversibly binding with streptavidinT. Yamamoto, K. Aoki, A. Sugiyama, H. Doi, T. Kodama, Y. Shimizu,* M. Kanai*Chem. Asian J. 2015, 10, 1071-1078. DOI: 10.1002/asia.201500120

20. Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component
Oxyarylation of Allenes
T. Itoh, Y. Shimizu,* M. Kanai*Org. Lett. 2014, 16, 2736-2739. DOI: 10.1021/ol501022d*Featured by SYNFACTS: Synfacts 2014, 10, 733. DOI: 10.1055/s-0034-1378287
21. Catalytic enantioselective synthesis of 2-(2-hydroxyethyl)indole scaffolds via
consecutive intramolecular amido-cupration of allenes and asymmetric addition ofcarbonyl compounds
P. K. Chikkade, Y. Shimizu, M. Kanai*Chem. Sci. 2014, 5, 1585-1590. DOI: 10.1039/C3SC52803K

22. A Catalytic C-C Bond-Formation with Minimal Use of Protecting Groups:
Construction of Functionalized Isotetronic Acid Derivatives
Y. Shimizu,* K. Yasuda, M. Kanai*
HETEROCYCLES 2014, 88, 919-927. DOI: 10.3987/COM-13-S(S)81

23. Catalytic Anomeric Aminoalkynylation of Unprotected Aldoses
Y. Kimura, S. Ito, Y. Shimizu, M. Kanai*Org. Lett. 2013, 15, 4130-4133. DOI: 10.1021/ol401810b

24. In situ Catalytic Generation of Allylcopper Species for Asymmetric Allylation:
Toward 1H-Isochromene Skeletons
J. Kawai, P. K. Chikkade, Y. Shimizu,* M. Kanai*

Angew. Chem. Int. Ed. 2013, 52, 7177-7180. DOI: 10.1002/anie.201302027*Featured by SYNFACTS: Synfacts 2013, 9, 1080. DOI: 10.1055/s-0033-1339830
25. Copper(I)-Catalyzed

Enantioselective

IncorporationofKetones

Hemiaminals for the Synthesis of Versatile Alkaloid Precursors
S. –L. Shi, X. –F. Wei, Y. Shimizu, M. Kanai*

J. Am. Chem. Soc. 2012, 134, 17019-17022. DOI: 10.1021/ja308872z

26. Cu(I)-catalyzed α-alkylation of ketones with styrene derivatives
S. Majima, Y. Shimizu,* M. Kanai*

Tetrahedron Lett. 2012, 53, 4381-4384. DOI: 10.1016/j.tetlet.2012.06.019

27. Catalytic Asymmetric Total Synthesis of ent-Hyperforin
Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai,* M. Shibasaki*

Angew. Chem. Int. Ed. 2010,49, 1103-1106. DOI: 10.1002/anie.200906678

toCyclic*Featured by SYNFACTS: Synfacts 2010, 5, 510. DOI: 10.1002/anie.200906678
28. The First Catalytic Asymmetric Total Synthesis of ent-Hyperforin
Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, M.* Shibasaki*

Tetrahedron 2010, 66, 6569-6584. DOI: 10.1016/j.tet.2010.05.086

29. Catalytic Asymmetric Synthesis of R207910
Y. Saga, R. Motoki, S. Makino, Y. Shimizu, M. Kanai,* M. Shibasaki*

J. Am. Chem. Soc. 2010, 132, 7905-7907. DOI: 10.1021/ja103183r

30. Asymmetric Reductive Mannich Reaction to Ketimines Catalyzed by a Cu(I)
ComplexY. Du, L. W. Xu, Y. Shimizu, K. Oisaki, M. Kanai,* M. Shibasaki*

J. Am. Chem. Soc. 2008, 130, 16146-16147. DOI: 10.1021/ja8069727

31. A new approach for the construction of a highly congested bicyclic system inpolycyclic polyprenylated acylphloroglucinols (PPAPs)
Y. Shimizu, A. Kuramochi, H. Usuda, M. Kanai,* M. Shibasaki*

Tetrahedron Lett. 2007, 48, 4173-4177. DOI: 10.1016/j.tetlet.2007.04.080

Accounts and Review
1. Carbon–Carbon Bond-Formations Promoted by Redox-Active Metal Catalysts
M. Kanai,* S. Matsunaga, K. Oisaki, Y. Shimizu

J. Synth. Org. Chem. Jpn. 2013, 71, 433-442. DOI: 10.5059/yukigoseikyokaishi.71.433
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
3. Recent progress in copper-catalyzed difunctionalization of unactivated carbon-carbon
multiple bonds
Y. Shimizu*, M. Kanai*

Tetrahedron Lett. 2014, 55, 3727-3737. DOI: 10.1016/j.tetlet.2014.05.077
4. Catalytic Asymmetric Addition Reactions of Cu(I)-Conjugated Soft Carbon
Nucleophiles
X.-F. Wei, Y. Shimizu, M. Kanai*Topics in Organometallic Chemistry 2015, 58, 169-182. DOI: 10.1007/3418_2015_163
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.
(http://www.chemistry.or.jp/journal/ci1810.pdf)
6. Development of Copper-Catalyzed Chemoselective Reactions
Yohei Shimizu

Chem. Pharm. Bull. 2019, xx, xx-xx. 奨励賞受賞記念 review
7. Cupid and Psyche system for the diagnosis and treatment of advanced cancer
A. Sugiyama, T. Kawamura, T. Tanaka, H. Doi, T. Yamashita, K. Shinoda, H. Fujitani,
K. Yamatsugu, Y. Shimizu, T. Tatsumi, K. Takahashi, M. Kanai, E. Mizohata, T.
Kawato, T. Doi, T. Inoue, T. Kodama

Proc. Jpn. Acad., Ser. B 2019, 95, 602–611.
Lectures1. ent-Hyperforin の触媒的不斉全合成
10.09.25 @ 若手研究者のためのセミナー(2010) (依頼公演)
千葉大学
2. Copper-Catalyzed C-C Bond Forming Reactions Utilizing Its “Soft” Characteristics
14.07.14 @ University of Alberta, Edmonton, Canada
Hosted by Professor Dennis Hall3. 保護基フリー合成を目指した化学選択的反応の開発

15.10.04 @ 有機触媒若手セミナー（名古屋） (依頼公演)
4. 触媒の特性を活かした化学選択的反応の開発
16.11.05 @ Hoshi University
第 40 回 星薬科大学大学院研究科助手会・大学院自治会 合同公開セミナー (invited)
5. ホウ素触媒によるカルボン酸の化学選択的求核的活性化法の開発
17.03.25 @ 有機合成化学の若い力
日本薬学会 第 137 年会（仙台） (invited)
6. Chemoselective C-C Bond Forming Reactions
17.04.06 @ Chalmers University of Technology, Göteborg, Sweden
Hosted by Professor Sture Lindegren
7. Chemoselective C-C Bond Forming Reactions
17.06.30 @ UCSB, California, USA
Hosted by Professor Armen Zakarian
8. 触媒の特性を活かした化学選択的反応の開発
17.07.08 @平成 29 年度若手研究者のためのセミナー (invited)
東京大学薬学系総合研究棟 2 階講堂
9. 触媒の特性を活かした化学選択的反応の開発
17.11.28 @第 12 回神戸大学有機反応化学研究会 (invited)
神戸大学理学部
Hosted by Associate Prof. Ryosuke Matsubara
10. 一価銅触媒の特性を活かした化学選択的反応の開発
17.11.29 @第二回有機若手ワークショップ (invited)京都大学理学研究科セミナーハウス
11. 一価銅触媒の特性を活かした化学選択的反応の開発
18.3.21 @日本化学会 第 98 春季年会 若い世代の特別講演会 （受賞講演）
日本大学船橋キャンパス
12. 触媒の特性を活かした化学選択的反応の開発
18.11.08 @若手研究者のための有機化学札幌セミナー (invited)北海道大学薬学部臨床薬学講義室
13. 触媒の特性を活かした化学選択的反応の開発
19.03.21@日本薬学会第 139 年会 （受賞講演）
ホテルニューオータニ幕張
14. Carboxylic Acid-Selective Enolate Formation
19.07.02@ Hokkaido Summer Symposium 2019 on Catalysis for Organic Synthesis(invited)
Hokkaido University Conference Hall, Sapporo, Japan15. Boron-Catalyzed α-Functionalization of Carboxylic Acids
19.11.15@ Hokkaido mini-Symposium by Young Generations in Asia (invited)
Hokkaido University, Sapporo, Japan