Article
Chemistry, Organic
Joanna C. Lee, James D. Cuthbertson, Nicholas J. Mitchell
Summary: We report the photocatalytic C2-alkylation of tryptophan using bromodifluoroacetate/acetamide-derived radical precursors. This reaction is rapid, additive-free, operationally simple, and tolerates diverse functionality. It enables late-stage modification of a variety of complex peptides, including examples of biological significance.
Article
Chemistry, Multidisciplinary
Qiqiang Xie, Guangbin Dong
Summary: Boron-homologation reactions offer an efficient and programmable method for the synthesis of alkylboronates, providing valuable and versatile synthetic intermediates. By implementing aza-Matteson reactions, selective mono- and double-methylene insertions can be achieved, allowing access to various alpha- and beta-boron-substituted tertiary amines. Additionally, derivatization of complex amine-containing bioactive molecules, diverse functionalization of boronate products, and sequential insertions of different carbenoids have all been successfully demonstrated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Reyner D. Vargas, Yuxuan Ding, Hallie O. Trial, Rouyu Qian, Zachary T. Ball
Summary: This study explores a catalytic proximity-induced methodology for covalent modification of glycopeptides using boronic acids as a saccharide recognition element, providing a new approach for saccharide recognition.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Julia O. Strelnikova, Nikolai Rostovskii, Olesya Khoroshilova, Alexander F. Khlebnikov, Mikhail S. Novikov
Summary: A high-yielding method for synthesizing 2H-1,3,5-oxadiazines by the rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with alpha-diazo esters has been developed, where the N2-attack and N4-attack of the carbenoid cause different oxadiazole ring openings controlled by the substitution at C5.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Hisanori Nambu, Ryoya Amano, Takafumi Tamura, Takayuki Yakura
Summary: This study describes the dirhodium(II)-catalyzed intramolecular insertion of aryldiazoacetates into unactivated primary C-H bonds. The reaction shows high selectivity and provides a direct route to 2-unsubstituted indane-1-carboxylates and specific isomers with ortho-substituted groups. Furthermore, a chemoselective C-H insertion reaction of aryldiazoacetate with a 1-oxyethyl substituent is achieved using a specific protecting group.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Chuan Wan, Yuena Wang, Chenshan Lian, Qi Chang, Yuhao An, Jiean Chen, Jinming Sun, Zhanfeng Hou, Dongyan Yang, Xiaochun Guo, Feng Yin, Rui Wang, Zigang Li
Summary: This study develops a novel visible-light-driven thioacetal activation reaction for facile modification of histidine residues. The method allows chemo-selective modification on peptides and proteins, enabling efficient histidine-proteome profiling. 78 histidine containing proteins were found for the first time, most of which function in metal accumulation in brain related diseases.
Article
Chemistry, Multidisciplinary
Fen Wang, Jierui Jing, Yanliang Zhao, Xiaohan Zhu, Xue-Peng Zhang, Liujie Zhao, Panjie Hu, Wei-Qiao Deng, Xingwei Li
Summary: This paper describes an asymmetric [3+2] annulation reaction of arylnitrones with different classes of alkynes catalyzed by chiral rhodium(III) complexes, resulting in the construction of three classes of chiral indenes/indenones. The coupling system features mild reaction conditions, excellent enantioselectivity, and high atom-economy, producing atropochiral pentatomic biaryls with C-centered point-chirality in excellent enantio- and diastereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Aoife M. Buckley, Daniel C. Crowley, Thomas A. Brouder, Alan Ford, U. B. Rao Khandavilli, Simon E. Lawrence, Anita R. Maguire
Summary: A new class of dirhodium carboxylate catalysts, derived from specific 2-fenchyloxy or 2-menthyloxy arylacetic acids, have shown excellent enantioselectivity and trans diastereoselectivity across a range of transformations. These catalysts are highly efficient in various reactions, such as C-H insertion, intramolecular aromatic addition, and oxonium ylide formation and rearrangement, displaying up to 93% ee in product yield.
Article
Biochemistry & Molecular Biology
Yulia A. Antonova, Yulia V. Nelyubina, Sema L. Ioffe, Andrey A. Tabolin
Summary: A Rh(II)-catalyzed reaction of cyclic nitronates with vinyl diazoacetates proceeds as an annulation reaction, producing bicyclic unsaturated nitroso acetals. Optimization of reaction conditions revealed the use of Rh(II) octanoate as the preferred catalyst in THF at room temperature, allowing the preparation of target products in good yields and excellent diastereoselectivity. Under basic conditions, these nitroso acetals undergo ring contraction into the corresponding pyrroles, and both transformations can be performed in a one-pot fashion.
Article
Chemistry, Organic
Miriam Ruiz-Serrano, Pilar Lopez-Alvarado, J. Carlos Menendez
Summary: Researchers found that the reaction between an a-formylcyclohexanone derivative and tosyl azide, in the presence of rhodium trifluoroacetate dimer, produced an acylsulfonamide derivative. This transformation is proposed to occur through a domino mechanism involving the in situ generation of an a-diazoketone, which is then transformed into a rhodium carbenoid and combined with N-tosylformamide, a side product of the first step. Overall, this transformation results in the formation of a C-N bond between the formyl carbon and the azide nitrogen adjacent to the sulfonyl group.
Review
Chemistry, Multidisciplinary
Santosh Kumar Sahu, Pradyota Kumar Behera, Prabhupada Choudhury, Madhusudan Sethi, Satyaban Jena, Laxmidhar Rout
Summary: This study summarizes the stereochemical outcomes of [3+2] cycloaddition using rhodium carbene-mediated diazo decomposition for highly diastereoselective poly oxacarbocycles formation. Further exploration with other transition metals and ylides is needed for synthesis of bridged polyheterocycles with potential drug candidate structures similar to known compounds like anthecularin, artemisinin, englerin and intracarene. This review presents a future outlook for organic chemists to explore the synthesis of bridged polyheterocarbocycles.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Yan Zhu, Ying Shao, Shengbiao Tang, Jiangtao Sun
Summary: A novel dearomative 1,4-rearrangement reaction of 2-carbonateindoles with aryl diazoacetates has been developed in the presence of a copper catalyst, leading to the formation of rearrangement products with an all-carbon quaternary center and two newly formed C-C bonds. This reaction involves the disruption of indole aromaticity and 1,4-carboxylate rearrangements.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Yuyang Dong, Alexandra T. Wrobel, Gerard J. Porter, Jessica J. Kim, Jake Z. Essman, Shao-Liang Zheng, Theodore A. Betley
Summary: Intramolecular alkoxylation of C-H bonds can introduce structural complexity rapidly. This study demonstrates a method using iron acetylacetonate as a catalyst for the preparation of oxacycles from alpha-diazo-beta-ketoesters. The reaction proceeds through a radical mechanism and provides access to complex structures under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Tiantian Feng, Yihui Yuan, Shilei Zhao, Lijuan Feng, Bingjie Yan, Meng Cao, Jiacheng Zhang, Wenyan Sun, Ke Lin, Ning Wang
Summary: The detection of environmental uranyl is a topic of increasing interest. This study presents a detection strategy based on the unique uranyl-triggered photocleavage property, using fluorescent-molecule-labelled protein fragments to achieve high selectivity and a low detection limit of 24 pM for uranyl detection. The method shows high reliability and stability, making it promising for practical applications in diverse environments.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Raffaele Senatore, Monika Malik, Thierry Langer, Wolfgang Holzer, Vittorio Pace
Summary: The study reports a formal CH2-CH2 homologation conducted with C1 carbenoids on a carbon electrophile for the obtainment of a four-membered cycle, resulting in the assembling of a rare imino-thietane cluster. The double homologation protocol demonstrates genuine chemocontrol and is accomplished directly on a carbon electrophile without the need for heteroatom-centered manifolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
