PUBLICATIONS
Original Papers
2025
Synthesis of N-Methyl Secondary Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Condensation of Carboxylic Acids with Aqueous Methylamine
Hinata Iwasawa, Naoya Takahashi, and Naoyuki Shimada*
A Unified Strategy for the Concise Total Syntheses of All Six 3′′-O-Acyl Quercitrins Based on Regioselective Acylation Catalyzed by Boronic Acid
Mari Tanikawa, Toshihiro Ishida, Yuki Nakamura, Kazuishi Makino, and Naoyuki Shimada*
2024
Organoboron Catalysis for Direct Amide/Peptide Bond Formation
Masayoshi Koshizuka, Naoya Takahashi and Naoyuki Shimada*
Chem. Comm. 2024, 60, 11202–11222. (Feature Article, Golden Open Access)
Selected as ChemComm 60th Anniversary Collection
Selected as Front Cover
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Boronic Acid/Palladium Hybrid Catalysis for Regioselective O-Allylation of Carbohydrates
Yuki Nakamura, Kazuma Irisawa, Kazuishi Makino, and Naoyuki Shimada*
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Hydroxy-Directed Peptide Bond Formation From α-Amino Acid-Derived Inert Esters Enabled by Boronic Acid Catalysis
Naoya Takahashi, Airi Takahashi, and Naoyuki Shimada*
Catalytic Dehydrative Amide Bond Formation Using Aqueous Ammonia: Synthesis of Primary Amides Utilizing Diboronic Acid Anhydride Catalysis
Naoya Takahashi, Hinata Iwasawa, Tatsuhito Kinashi, Kazuishi Makino, and Naoyuki Shimada*
Chem. Commun. 2023, 59, 7391–7394.
Selected as ChemComm Milestones-First Independent Articles.
Concise Synthesis of 2,5-Diketopiperazines via Catalyatic Hydroxy-Directed Peptide Bond Formations
Masayoshi Koshizuka, Kaito Shinoda, Kazuishi Makino, and Naoyuki Shimada*
2021
Direct Synthesis of N -Protected Serine- and Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of Garner's Aldehyde
Naoyuki Shimada, * Naoki Ohse, Naoya Takahashi, Sari Urata, Masayoshi Koshizuka, and Kazuishi Makino
Highlighted in a News Article for SynForm.
Boronic Acid-Catalyzed Regioselective Koenigs–Knorr-Type Glycosylation
Naoyuki Shimada, * Tomoya Sugimoto, Mao Noguchi, Chikako Ohira, Yutaro Kuwashima, Naoya Takahashi, Noriko Sato, and Kazuishi Makino
Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3'-Acyl Bisabolol b- D -Fucopyranoside Natural Products and Their Analogues
Yuki Nakamura, Takayuki Ochiai, Kazuishi Makino, and Naoyuki Shimada *
Chem. Pharm. Bull. 2021 , 69, 281–285.
Selected as Front Cover & Featured Articles.
2020
Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation
Masayoshi Koshizuka, Kazuishi Makino, and Naoyuki Shimada *
Synthesis of Weinreb Amides Using Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation of Carboxylic Acids
Naoyuki Shimada, * Naoya Takahashi, Naoki Ohse, Masayoshi Koshizuka, and Kazuishi Makino
2019
An Efficient Deprotection of 2,6-Bis (trifluoromethyl) phenylboronic Esters via Catalytic Protodeboronation Using Tetrabutylammonium Fluoride
Sari Urata, Shinya Nojima, Kazuishi Makino, and Naoyuki Shimada *
Total Syntheses of Seminolipid and Its Analogues by Using 2,6-Bis (trifluoromethyl) phenylboronic Acid as Protective Reagent
Naoyuki Shimada, * Kenji Fukuhara, Sari Urata, and Kazuishi Makino *
Diboronic Acid Anhydrides as Effective Catalysts for the Hydroxyl-Directed Dehydrative Amidation of Carboxylic Acids
Naoyuki Shimada, * Mai Hirata, Masayoshi Koshizuka, Naoki Ohse, Ryoto Kaito, and Kazuishi Makino
Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates
Naoyuki Shimada, * Yuki Nakamura, Takayuki Ohiai, and Kazuishi Makino
2018
2,6-Bis (trifluoromethyl) phenylboronic Esters as Protective Groups for Diols: A Protection / Deprotection Protocol for Use under Mild Conditions
Naoyuki Shimada, * Sari Urata, Kenji Fukuhara, Takao Tsuneda, and Kazuishi Makino *
Org. Lett. 2018 , 20, 6064–6068.
Selected as Most Read Articles ”Monthly top 20 Articles” rank # 6.
2017
Deprotection of Silyl Ethers by Using SO3H Silica Gel: Application to Sugar, Nucleoside, and Alkaloid Derivatives
Hideaki Fujii, * Naoyuki Shimada, Masaki Ohtawa, Fumika Karaki, Masayoshi Koshizuka, Kohei Hayashida, Mitsuhiro Kamimura, Kazuishi Makino, Tohru Nagamitsu, and Hiroshi Nagase
Tetrahedron 2017 , 73, 5425–5429.
2016
Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid
Kenji Fukuhara, Naoyuki Shimada, Takashi Nishino, Eisuke Kaji, * and Kazuishi Makino *
University of Hawaii / The Tius Research Group
C1'-Azacycloalkyl Hexahydrocannabinols
Thanh C. Ho, Naoyuki Shimada, Marcus A. Tius, * Spyros P. Nikas, Wen Zhang, and Alexandros Makriyannis *
Enantioselective Palladium (0)-Catalyzed Nazarov-Type Cyclization
Kei Kitamura, Naoyuki Shimada, Craig Stewart, Abdurrahman C. Atesin, Tülay A. Ateşin, * and Marcus A. Tius *
Neutral Nazarov-Type Cyclization Catalyzed by Palladium (0)
Naoyuki Shimada, Craig Stewart, William F. Bow, Anais Jolit, Kahoano Wong, Zhe Zhou, and Marcus A. Tius *
An Organocatalytic Asymmetric Nazarov Cyclization
Ashok K. Basak, Naoyuki Shimada, William F. Bow, David A. Vicic, and Marcus A. Tius *
Organocatalytic Asymmetric Aza-Nazarov Cyclization of an Azirine
Naoyuki Shimada, Bradley O. Ashburn, Ashok K. Basak, William F. Bow, David A. Vicic, and Marcus A. Tius *
Hokkaido University / The Hashimoto Research Group
Asymmetric Total Synthesis of (–)-Engrelin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition
Taiki Hanari, Naoyuki Shimada, Yasunobu Kurosaki, Neetipalli Thrimurtulu, Hisanori Nambu, Masahiro Anada, * and Shunichi Hashimoto *
Enantio- and Diastereoselctive Hetero-Diels–Alder Reactions Between 4-Methyl-Substituted Rawal's Diene and Aldehydes Catalyzed by Chiral Dirhodium (II) Carboxylates: Catalytic Asymmetric Synthesis of (–)-cis-Aerangis Lactone
Yudai Watanabe, Naoyuki Shimada, Masahiro Anada, and Shunichi Hashimoto *
Continuous Flow System with a Polymer-Supported Dirhodium (II) Catalyst: Application to Enantioselective Carbonyl Ylide Cycloaddition Reactions
Koji Takeda, Tadashi Oohara, Naoyuki Shimada, Hisanori Nambu, and Shunichi Hashimoto *
Chem. Eur. J. 2011 , 17, 13992–13998.
Highlighted in Synfacts 2012 , 8, 337 & Selected as the SYNFACT of the month.
Catalytic Enantioselective Intermolecular Cycloaddition of Diketoester-Derived Carbonyl Ylides with Indoles Using Chiral Dirhodium (II) Carboxylates
Naoyuki Shimada, Tadashi Oohara, Janagiraman Krishnamurthi, Hisanori Nambu, and Shunichi Hashimoto *
Highly Enantioselective Cyclopropenation Reaction of 1-Alkynes with α-Alkyl-α-Diazoesters Catalyzed by Dirhodium (II) Carboxylates
Takayuki Goto, Koji Takeda, Naoyuki Shimada, Hisanori Nambu, Masahiro Anada, Motoo Shiro, Kaori Ando, and Shunichi Hashimoto *
Catalytic Asymmetric Synthesis of Descurainin via 1,3-Dipolar Cycloaddition of a Carbonyl Ylide Using Rh 2 (R-TCPTTL) 4
Naoyuki Shimada, Taiki Hanari, Yasunobu Kurosaki, Masahiro Anada, Hisanori Nambu, and Shunichi Hashimoto *
Catalytic Asymmetric Synthesis of the endo-6-Aryl-8-oxabicyclo [3.2.1] oct-3-en-2-one Natural Product from Ligusticum Chuanxing via 1,3-Dipolar Cycloaddition of a Formyl-Derived Carbonyl Ylide Using Rh 2 (S-TCPTTL) 4
Naoyuki Shimada, Taiki Hanari, Yasunobu Kurosaki, Koji Takeda, Masahiro Anada, Hisanori Nambu, Motoo Shiro, and Shunichi Hashimoto *
J. Org. Chem. 2010 , 75, 6039–6042.
Highlighted in Synfacts 2010 , 1329 & Selected as the SYNFACT of the month.
Catalytic Asymmetric Construction of the exo-7-Aryl-6,8-dioxabicyclo [3.2.1] octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy
Yasunobu Kurosaki, Naoyuki Shimada, Masahiro Anada, Hisanori Nambu, Motoo Shiro, and Shunichi Hashimoto *
Bull. Korean Chem. Soc. 2010 , 31, 694–696. (Special Issue)
Highly Enantioselective Hetero-Diels–Alder Reactions Between Rawal's Diene and Aldehydes Catalyzed by Chiral Dirhodium (II) Carboxamidates
Yudai Watanabe, Takuya Washio, Naoyuki Shimada, Masahiro Anada, and Shunichi Hashimoto *
Enantioselective Construction of 2,8-Dioxabicyclo [3.2.1] octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylides Using Chiral Dirhodium (II) Carboxylates
Naoyuki Shimda, Masahiro Anada, Motoo Shiro, and Shunichi Hashimoto *
Chem. Lett. 2009 , 38, 488–489. ( Special Issue ) (Dedicated to Professor Ryoji Noyori on the occacion of his 70th birthday)
Asymmetric Formal Synthesis of (–)-Pancracine via Catalytic Enantioselective C–H Amination Process
Masahiro Anada, Masahiko Tanaka, Naoyuki Shimada, Hisanori Nambu, Minoru Yamawaki, and Shunichi Hashimoto *
Asymmetric Approach to the Pentacyclic Skelton of Aspidosperma alkaloids via Enantioselective 1,3-Dipolar Cycloaddition of Carbonyl Ylides Catalyzed by Chiral Dirhodium (II) Carboxylates
Hisanori Nambu, Mayuka Hikime, Janagiraman Krishnamurthi, Megumi Kamiya, Naoyuki Shimada, and Shunichi Hashimoto *
Catalytic Enantioselective Intermolecular Cycloaddition of 2-Diazo-3,6-diketoesters-Derived Carbonyl Ylides with Alkynes and Styrenes Using Chiral Dirhodium (II) Carboxylates
Naoyuki Shimada, Masahiro Anada, Seiichi Nakamura, Hisanori, Nambu, Hideyuki Tsutsui, and Shunichi Hashimoto *
Catalytic Enantioselective Tandem Carbonyl Ylide Formation / 1,3-Dipolar Cycloaddition of a-Diazo Ketones with Aromatic Aldehydes Using Dirhodium (II) Tetrakis [N-benzene-fused-phthaloyl- (S) -valinate]
Hideyuki Tsutsui, Naoyuki Shimada, Takumi Abe, Masahiro Anada, Makoto Nakajima, Seiichi Nakamura, Nambu Hisanori and Shunichi Hashimoto *
A New Dirhodium (II) Carboxylate Complex as a Chiral Lewis Acid Catalyst for Enantioselective Hetero-Diels–Alder Reactions
Masahiro Anada, Takuya Washio, Naoyuki Shimada, Shinji Kitagaki, Makoto Nakajima, Motoo Shiro, and Shunichi Hashimoto *
Nihon University / The Shimizu Research Group
Mannich-Type Reactions in Water Using Anionic Water-soluble Calixarenes as Recoverable and Reusable Catalysts
Shoichi Shimizu, * Naoyuki Shimada, and Yasuyuki Sasaki
Reviews & Accounts
Organoboron Catalysis for Direct Amide/Peptide Bond Formation
Masayoshi Koshizuka, Naoya Takahashi and Naoyuki Shimada*
Chem. Comm. 2024, Advanced Article (Feature Article)
Selected as ChemComm 60th Anniversary Collection
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Asymmetric Nazarov Cyclizations
Naoyuki Shimada, Craig Stewart, and Marcus A. Tius *
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Books & Highlights etc.
2,6-Bis(trifluoromethyl)phenylboronic Acid
Naoyuki Shimada,* and Kazuishi Makino
e-EROS: Encyclopedia of Reagents for Organic Synthesis
キラルなチオウレアとアキラルなチオウレアの協奏機能触媒作用
嶋田 修之