PUBLICATIONS
Original Papers
2024
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 β-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 Rh2(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 Rh2(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
Asymmetric Nazarov Cyclizations
Naoyuki Shimada, Craig Stewart, and Marcus A. Tius*
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Books & Highlights etc.
アミド化
嶋田 修之
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