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

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.

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.

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.

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*

J. Org. Chem. 2023, 88, 6901–6910.

Highlighted in Synfacts 2023, 19, 844.

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.

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.

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*

Org. Lett. 2020, 22, 8658–8664.

Highlighted in Synfacts 2021, 17, 107.

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.

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.

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.

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.

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.

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*

Eur. J. Org. Chem. 2016, 902–905.

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.

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.

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.

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.

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.

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.

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.

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*

Org. Lett. 2011, 13, 6284–6287.

Highlighted in Synfacts 2012, 8, 294.

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.

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*

Tetrahedron Lett. 2010, 51, 6572–6575.

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*

Chem. Commun. 2009, 45, 7294–7296.

Highlighted in Synfacts 2010, 324.

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*

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

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.

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.

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.