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PUBLICATIONS

Original Papers

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*

J. Org. Chem. 2024, ​89, 1320–1330.

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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*

Chem. Commun. 2024, 60, 448–451.

Highlighted in Synfacts 2024, 20, 324.

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2023

 

ジボロン酸無水物触媒による脱水縮合アミド化反応の開発

嶋田 修之

有機合成化学協会誌 2023, 81, 668–680.

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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.

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Concise Synthesis of 2,5-Diketopiperazines via Catalyatic Hydroxy-Directed Peptide Bond Formations

Masayoshi Koshizuka, Kaito Shinoda, Kazuishi Makino, and Naoyuki Shimada*

J. Org. Chem. 2023, 88, 6901–6910.

Highlighted in Synfacts 2023, 19, 844.

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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

Synlett 2021, 32 , 1024–1028.

Highlighted in a News Article for SynForm.

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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

J. Org. Chem. 2021, 86, 5973–5982.

Highlighted in Synfacts 2021 , 17, 627.

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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.

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2020

 

Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation

Masayoshi Koshizuka, Kazuishi Makino, and Naoyuki Shimada *

Org. Lett. 2020 , 22, 8658–8664.

Highlighted in Synfacts 2021 , 17, 107.

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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

Chem. Commun. 2020 , 56, 13145–13148.

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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 *

Synlett 2019 , 30, 2300–2304.

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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 *

Org. Biomol. Chem. 2019 , 17, 7325–7329.

Selected as Total Synthesis in OBC 2019 .

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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

Org. Lett. 2019 , 21, 4303–4308.

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Catalytic Activation of Cis-Vicinal Diols by Boronic Acids: Site-Selective Acylation of Carbohydrates

Naoyuki Shimada, * Yuki Nakamura, Takayuki Ohiai, and Kazuishi Makino

Org. Lett. 2019 , 21, 3789–3794.

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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.

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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.

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2016

 

Regioselective, Tin-Free Sulfation of Unprotected Hexopyranosides by Using Phenylboronic Acid

Kenji Fukuhara, Naoyuki Shimada, Takashi Nishino, Eisuke Kaji, * and Kazuishi Makino *

Eur. J. Org. Chem. 2016 , 902–905.

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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 *

J. Org. Chem. 2017 , 82, 7839–7849.

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Enantioselective Palladium (0)-Catalyzed Nazarov-Type Cyclization

Kei Kitamura, Naoyuki Shimada, Craig Stewart, Abdurrahman C. Atesin, Tülay A. Ateşin, * and Marcus A. Tius *

Angew. Chem. Int. Ed. 2015 , 54, 6288–6291.

Highlighted in Synfacts 2015 , 11, 845.

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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 *

Angew. Chem. Int. Ed. 2012 , 51, 5727–5729.

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An Organocatalytic Asymmetric Nazarov Cyclization

Ashok K. Basak, Naoyuki Shimada, William F. Bow, David A. Vicic, and Marcus A. Tius *

J. Am. Chem. Soc. 2010 , 132, 8266–8267.

Highlighted in Synfacts 2010 , 953.

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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 *

Chem. Commun. 2010 , 46, 3774–3775.

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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 *

Chem. Eur. J. 2015 , 17, 13992–13998.

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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 *

Tetrahedron: Asymmetry 2014 , 25, 63–73.

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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.

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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 *

Org. Lett. 2011 , 13, 6284–6287.

Highlighted in Synfacts 2012 , 8, 294.

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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 *

Angew. Chem. Int. Ed. 2011 , 50, 6803–6808.

Highlighted in Synfacts 2011 , 1084.

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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 *

Tetrahedron Lett. 2010 , 51, 6572–6575.

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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.

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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)

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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 *

Chem. Commun. 2009 , 45, 7294–7296.

Highlighted in Synfacts 2010 , 324.

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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)

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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 *

Tetrahedron 2009 , 65, 3069–3077. (Special Issue)

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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 *

Tetrahedron Lett. 2009 , 50, 3675–3678.

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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 *

Org. Lett. 2008 , 10, 3603–3606.

Highlighted in Synfacts 2008 , 1069.

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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 *

Adv. Synth. Catal. 2007 , 349, 521–526.

Highlighted in Synfacts 2007 , 827.

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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 *

Angew. Chem. Int. Ed. 2004 , 43, 2665–2668.

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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

Green Chem. 2006 , 8, 608–614.

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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 *

Tetrahedron 2011 , 67, 5851–5870.

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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

ファルマシア 2012, 48, 791.

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