Article
Chemistry, Multidisciplinary
Lei Wang, Lifan Wang, Mingxia Li, Qinglei Chong, Fanke Meng
Summary: A novel cobalt-catalyzed reaction has been introduced in this article, which efficiently introduces allyl groups into molecules with stereoselective formation of diversified enantioenriched homoallylic alcohols. The mechanism involves allyl radical intermediates and represents a new strategy for enantioselective transformations using chiral Co complexes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Jie Chen, Dong-yu Zhu, Xue-jing Zhang, Ming Yan
Summary: An enantioselective Michael addition has been developed for the synthesis of structurally diverse isatin-derived alpha-(trifluoromethyl)imine derivatives with excellent yields and enantioselectivities, which are valuable candidates for drug discovery.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Laura Carceller-Ferrer, Carlos Vila, Gonzalo Blay, M. Carmen Munoz, Jose R. Pedro
Summary: A valuable organocatalytic vinylogous Mannich reaction has been established between alkylidenepyrazolones and isatin-derived ketimines. The reaction was catalyzed by a squaramide organocatalyst, resulting in a range of aminooxindole-pyrazolone adducts with excellent outcomes, including high yields and selectivities.
Article
Chemistry, Multidisciplinary
Oliver D. Jackson, Ksenia S. Stankevich, Matthew J. Cook
Summary: An auto-tandem catalytic, branched-selective rearrangement of substituted N-alloc-N-allyl ynamides was developed, which provides an easy access to complex quaternary nitrile products with vinylogous stereocentres in excellent diastereoselectivity, including contiguous all-carbon quaternary centres. The stereochemical outcome is determined via a Pd(0) catalysed dipolar ketenimine aza-Claisen rearrangement, and computational studies illustrate the significant role of ligand geometry.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Tetsuya Kadota, Masanao Sawa, Yuta Kondo, Hiroyuki Morimoto, Takashi Ohshima
Summary: This study successfully achieved direct transformation of unprotected α-aminonitriles, streamlining the synthesis of unnatural amino acid derivatives and achieving the shortest one-pot stereoselective routes to a biologically active compound reported to date.
Article
Chemistry, Multidisciplinary
Yu-Han Lu, Si-Yu Mu, Hong-Xia Li, Jun Jiang, Chao Wu, Min-Hang Zhou, Wen-Tao Ouyang, Wei-Min He
Summary: By utilizing formaldehyde as an atom-economical carbonyl synthon, a novel EtOH-catalyzed electrochemical multicomponent synthesis of imidazolidine-fused sulfamidates was developed. The reaction provided a wide range of products in good to excellent yields under organic oxidant-free, energy-saving, and mild conditions. Mechanistic studies revealed that the in situ generated ethoxide played a crucial role in producing aminomethylene radicals at a lower voltage.
Article
Chemistry, Physical
Koji Kubota, Daiyo Miura, Takumi Takeuchi, Shun Osaki, Hajime Ito
Summary: The study introduces a novel catalytic enantioselective nucleophilic borylation reaction of ketimines, leading to the efficient synthesis of optically active alpha-amino tertiary boronates with high enantioselectivity. The products can be further converted into peptidylboronic acid derivatives that are difficult to synthesize by other methods. Density functional theory calculations suggest that noncovalent interactions play a crucial role in determining the enantioselectivity of this reaction.
Article
Chemistry, Physical
Ruijie Mi, Xuepeng Zhang, Jinlei Wang, Haohua Chen, Yu Lan, Fen Wang, Xingwei Li
Summary: This study reports the rhodium-catalyzed enantioselective three-component coupling of arene, diene, and dioxazolone via C-H activation to produce chiral allylic amines. The electrophilic amination of the pi-allyl species is both regio- and enantio-determining in this carboamination reaction.
Article
Chemistry, Organic
Jin-Rui Li, Yun Yao, Chong-Dao Lu
Summary: A stereocontrolled electrophilic amination approach was employed for the synthesis of α-aminoketone derivatives with less accessible α-tetrasubstituted stereocenters. Stereospecific α-deprotonation of ketimines followed by nucleophilic attack of azodicarboxylic derivatives afforded α-aminated products in high yields with excellent stereoselectivities.
Review
Chemistry, Multidisciplinary
Mary Sravani Galla, Darshana Bora, Nagula Shankaraiah
Summary: Sulphonamides and N-sulphonyl ketimines/aldimines have versatile applications in synthetic and medicinal chemistry, contributing to regioselectivity in C-H activation and functionalization reactions as directing groups. They also aid in site selectivity and late-stage functionalization of drug molecules for constructing complex therapeutic scaffolds through C-H activation.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Lei Dai, Xueting Zhou, Jiami Guo, Xuan Dai, Qingqin Huang, Yixin Lu
Summary: The C-N axially chiral N-arylpyrrole motifs are important scaffolds in biologically active compounds, but their asymmetric synthesis is challenging. In this study, the authors developed a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Hui Liu, Yingkun Yan, Min Li, Xiaomei Zhang
Summary: By utilizing chiral phosphoric acid as a catalyst, enantioselective aza-Friedel-Crafts reaction between 5-aminoisoxazoles and isatin-derived N-Boc ketimines was achieved, yielding novel 3-isoxazole 3-amino-oxindoles with high yields and moderate to good enantioselectivities. One product's absolute configuration was determined by X-ray crystal structural analysis, and a plausible reaction mechanism was proposed, followed by a successful scale-up reaction. Additionally, the product underwent Suzuki-Miyaura coupling with phenylboronic acid, resulting in moderate yield without affecting the enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Sooyun Choi, Melody C. Guo, Gavin M. Coombs, Scott J. Miller
Summary: An atroposelective synthesis method for N-aryl 1,2,4-triazoles was developed. By utilizing a chiral phosphoric acid catalyst, a cyclodehydration reaction achieved asymmetric induction, resulting in atropisomeric N-aryl 1,2,4-triazoles with up to 91:9 enantiomeric ratio. Further crystallization of the isolated heterocycle enhanced the atropisomeric ratio of several analogs to 99:1 or higher. Additionally, a divergent and substrate-dependent reaction pathway leading to a different heterocyclic product was revealed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Andres Arribas, Martin Calvelo, David F. Fernandez, Catarina A. B. Rodrigues, Jose L. Mascarenas, Fernando Lopez
Summary: The study presents a versatile and highly enantioselective intramolecular hydrocarbonation reaction for the synthesis of heteropolycyclic systems with chiral quaternary carbon stereocenters. The method relies on an iridium-(I)/bisphosphine chiral catalyst, yielding fused indole and pyrrole products with high enantiomeric excesses. DFT computational studies provided a detailed mechanistic profile and identified weak non-covalent interactions as key factors controlling the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yu-Xuan Su, Ming-Yao Huang, Shou-Fei Zhu
Summary: Amino acids, as the building blocks of proteins, play crucial roles in various fields such as synthetic chemistry, medicinal chemistry, and materials chemistry. While natural amino acids can be obtained from living organisms, synthetic methods are necessary for unnatural amino acids. A recent method utilizing asymmetric N-H bond carbene insertion reaction with α-diazoacetates has demonstrated high enantioselectivity and good functional group tolerance, enabling the facile synthesis of both natural and unnatural amino acids and introducing new concepts in catalysis.
Article
Chemistry, Multidisciplinary
J. Stephen Clark, Filippo Romiti, Kirsten F. Hogg, Malai Haniti S. A. Hamid, Sven C. Richter, Alistair Boyer, Joanna C. Redman, Louis J. Farrugia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
J. Stephen Clark, Filippo Romiti, Bora Sieng, Laura C. Paterson, Alister Stewart, Subhabrata Chaudhury, Lynne H. Thomas
Article
Multidisciplinary Sciences
Thach T. Nguyen, Ming Joo Koh, Xiao Shen, Filippo Romiti, Richard R. Schrock, Amir H. Hoveyda
Article
Multidisciplinary Sciences
Shaochen Zhang, Juan del Pozo, Filippo Romiti, Yucheng Mu, Sebastian Torker, Amir H. Hoveyda
Article
Chemistry, Multidisciplinary
Sota Akiyama, Koji Kubota, Malte S. Mikus, Paulo H. S. Paioti, Filippo Romiti, Qinghe Liu, Yuebiao Zhou, Amir H. Hoveyda, Hajime Ito
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Review
Chemistry, Multidisciplinary
Filippo Romiti, Juan del Pozo, Paulo H. S. Paioti, Stella A. Gonsales, Xinghan Li, Felix W. W. Hartrampf, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Applied
Kevin P. McGrath, Aran K. Hubbell, Yuebiao Zhou, Damian Padin Santos, Sebastian Torker, Filippo Romiti, Amir H. Hoveyda
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Multidisciplinary
Paulo H. S. Paioti, Juan del Pozo, Malte S. Mikus, Jaehee Lee, Ming Joo Koh, Filippo Romiti, Sebastian Torker, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Ryan J. Morrison, Farid W. van der Mei, Filippo Romiti, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Juan del Pozo, Shaochen Zhang, Filippo Romiti, Shibo Xu, Ryan P. Conger, Amir H. Hoveyda
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Yucheng Mu, Felix W. W. Hartrampf, Elsie C. Yu, Katherine E. Lounsbury, Richard R. Schrock, Filippo Romiti, Amir H. Hoveyda
Summary: This study introduces a new method for synthesizing trisubstituted macrocyclic olefins, which can produce stereoisomers and overcome unexpected difficulties. The effectiveness of the method is demonstrated through two examples.
Article
Chemistry, Organic
Filippo Romiti, Ludovic Decultot, J. Stephen Clark
Summary: This study presents a convergent synthetic route for the complete carbon framework of the macrocyclic marine natural product amphidinolide F, which involves coupling three fragments of similar size and complexity. Key features of the fragment syntheses include stereoselective construction of the tetrahydrofuran in the C1-C9 fragment, highly diastereoselective aldol reaction in the C10-C17 fragment, and intramolecular nucleophilic ring opening in the C18-C29 fragment.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shibo Xu, Juan del Pozo, Filippo Romiti, Yue Fu, Binh Khanh Mai, Ryan J. Morrison, KyungA Lee, Shaowei Hu, Ming Joo Koh, Jaehee Lee, Xinghan Li, Peng Liu, Amir H. Hoveyda
Summary: Molecules containing fluorine atoms are crucial for drug discovery, but synthesizing compounds with both trifluoromethyl- and fluoro-substituted stereogenic carbon center is challenging. This study presents a catalytic strategy for preparing homoallylic alcohols with these specific carbon centers.
Article
Chemistry, Multidisciplinary
Gujjula V. Ramakrishna, Larisa P. Pop, Zurwa Latif, Harish K. V. Suryadevara, Luca Santo, Filippo Romiti
Summary: This article presents a general, concise, and efficient strategy for the enantioselective synthesis of the eburnane alkaloid family, allowing the preparation of multiple members and facilitating further biological studies.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)