Article
Chemistry, Organic
Yuko Suzuki, Kazuya Kanemoto, Ayana Inoue, Kazumi Imae, Shin-ichi Fukuzawa
Summary: The asymmetric 1,3-dipolar cycloaddition of glycine imino esters to Morita-Baylis-Hillman (MBH) adducts or acetylated MBH adducts was efficiently catalyzed by AgOAc/(R,S-p)-ThioClickFerrophos to provide pyrrolidine derivatives with a quaternary carbon center as a single diastereomer with excellent enantioselectivity. Additionally, utilizing a cyclic pyrroline ester as the nucleophile in the tandem addition-elimination reaction with an acetylated MBH adduct resulted in the formation of an exo-olefin with high yield and enantioselectivity. The broad substrate scope and transformability of the products allow for rapid access to diverse multifunctionalized pyrrolidines in an optically pure manner.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Felipe Verdugo, Ricardo Rodino, Martin Calvelo, Jose Luis Mascarenas, Fernando Lopez
Summary: The reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) can be directed towards tandem cycloisomerization/cross-coupling processes by using Pd-0 catalysts with phosphorus-based monodentate ligands. This allows for the synthesis of a wide variety of highly functionalized cyclic alcohols and amines through the formation of key pi-allyl oxapalladacyclic intermediates which are trapped with external nucleophilic partners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Jyoti M. Honnanayakanavar, Purna Chandra Behera, Surisetti Suresh
Summary: This study discloses a copper-catalyzed tandem process that integrates N-arylation and 1,4-conjugate addition using cyclic enaminones and ortho-halochalcones as substrates, resulting in the formation of diverse tricyclic tetrahydroacridinone derivatives in moderate to excellent yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Caijin Zeng, Songjia Fang, Shuqi Guo, Huanfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel and efficient palladium-catalyzed annulation of anilines with bromoalkynes for the synthesis of 2-phenylindoles has been described. This approach features excellent regio- and stereoselectivities and good functional group tolerance. Preliminary mechanistic studies indicate that anilines undergo anti-nucleophilic addition to bromoalkynes to generate (Z)-N-(2-bromo-1-phenyl-vinyl) anilines, followed by sequential C-H functionalization to deliver different substituted 2-phenylindoles. This method provides potential applications for the construction of various biologically active compounds.
Article
Chemistry, Organic
Yu-Jie Li, De-Guang Liu, Jin-Hu Ren, Tian-Jun Gong, Yao Fu
Summary: Photocatalytic oxidation is a widely used method in organic synthesis, and has applications in both academia and industry. In this study, we developed a blue light-induced alkylation-oxidation tandem reaction for the synthesis of diverse ketones. This reaction shows excellent functional group compatibility and can be used with a variety of radical precursors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liher Prieto, Veronica Rodriguez, Jose L. Vicario, Efraim Reyes, Valentin Hornillos
Summary: A palladium-catalyzed asymmetric conjugate addition reaction of aryl boronic acids to medium-sized cycloalkenones followed by intramolecular aldol trapping has been reported. The catalyst, formed in situ as [Pd/(QuinoxP*)], enables the synthesis of arylbicyclic scaffolds with high yields and excellent stereocontrol (up to 7:1 dr, up to 99% ee). This reaction is applicable to various medium-sized ketoenone substrates and functionalized aryl boronic acids, including heterocyclic compounds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ping Zhang, Guo-Li Chai, En-Ze Yao, Li-Xiao Guo, Xue-Yu Liu, Junbiao Chang
Summary: Asymmetric conjugate addition of organic boronic acids to dienones was achieved using chiral catalysts, resulting in high yields of enantiopure bis-adducts with excellent chemoselectivities and enantioselectivities. These catalytic systems demonstrated high efficiency and broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Summary: In this study, the efficient synthesis of pyranones was achieved through a three-component cascade reaction under ruthenium catalysis using readily available acrylic acids, ethyl glyoxylate, and p-toluenesulfonamide. For the first time, the nucleophilic addition of the vinylic C-H bond of acrylic acids across aldehyde was achieved, followed by intramolecular cyclization and subsequent second insertion to aldehyde to form substituted butenolides. The sulfonamides were eliminated at higher temperature to yield the pyranones.
Article
Chemistry, Organic
Long Li, Jiao-Zhe Li, Yong-Bin Sun, Chun-Mei Luo, Hui Qiu, Keqi Tang, Hongxin Liu, Wen-Ting Wei
Summary: A novel visible-light-catalyzed tandem radical addition/1,5-hydrogen atom transfer/cyclization cascade reaction was developed for the synthesis of sulfonylfunctionalized dihydrobenzofurans. This reaction relies on unique energy transfer and solvent-radical relay strategies, enabling the generation of sulfonyl radicals under photocatalyst-and additive-free conditions.
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Physical
Taichi Yumura, Takeshi Nanjo, Yoshiji Takemoto
Summary: This article reports an efficient hybrid photo-redox catalyst that enables radical cyclization of unsaturated carboxylic acids previously requiring harsh reaction conditions. Mechanistic studies have revealed that the catalyst promotes single electron transfer and leads to unconventional cis-trans isomerization of the cyclobutane rings.
Article
Biochemistry & Molecular Biology
Anna N. Philippova, Daria V. Vorobyeva, Pavel S. Gribanov, Ivan A. Godovikov, Sergey N. Osipov
Summary: An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
Article
Chemistry, Organic
Wenwei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing-Yuan Ge, Ningning Lv, Jiuxi Chen
Summary: We report a novel pathway to synthesize gamma-lactams using acetonitrile analogues as coupling partners. This method does not require oxidants, ligands, and Lewis acids, and exhibits a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Multidisciplinary
Jinbin Zhu, Zhenyue Li, Jiaqi Li, Duanshuai Tian, Ronghua Xu, Zhiyong Tan, Zhengwang Chen, Wenjun Tang
Summary: In this report, an efficient rhodium-catalyzed addition of arylboronic acids to N-heteroaryl ketones is established, affording a variety of valuable alpha-heteroaryl alcohols with excellent functional group compatibility. The employment of the WingPhos ligand containing two anthryl groups is crucial for this transformation.
Article
Chemistry, Multidisciplinary
Sachin R. Shirsath, Sagar M. Chandgude, M. Muthukrishnan
Summary: An iron(III) catalyzed tandem ring opening/1,6-conjugate addition of cyclopropanols to p-quinone methides leading to gamma,gamma-diaryl ketones has been reported. This novel catalytic protocol provides an efficient method to access gamma,gamma-diaryl ketone derivatives with high yields and functional group tolerance. Importantly, these ketones can be further functionalized to generate a versatile set of useful products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
S. Roscales, A. G. Csaky
CHEMICAL COMMUNICATIONS
(2016)
Correction
Chemistry, Organic
Francisco Sanchez-Sancho, Aurelio G. Csaky
SYNTHESIS-STUTTGART
(2016)
Article
Chemistry, Organic
Victor Ortega, Estefania del Castillo, Aurelio G. Csaky
Article
Chemistry, Organic
Silvia Roscales, Aurelio G. Csaky
Article
Chemistry, Physical
Sara Llamas, Laura Fernandez-Pena, Andrew Akanno, Eduardo Guzman, Victor Ortega, Francisco Ortega, Aurelio G. Csaky, Richard A. Campbell, Ramon G. Rubio
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2018)
Editorial Material
Chemistry, Physical
Aurelio G. Csaky
Article
Chemistry, Organic
Silvia Roscales, Victor Ortega, Aurelio G. Csaky
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Silvia Roscales, Aurelio G. Csaky
JOURNAL OF CHEMICAL EDUCATION
(2019)
Article
Chemistry, Multidisciplinary
Silvia Roscales, Aurelio G. Csaky
Article
Chemistry, Applied
Silvia Roscales, Aurelio G. Csaky
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Multidisciplinary
Silvia Roscales, Aurelio G. Csaky
Summary: The method reported in the study utilizes nitrosobenzene as a reagent to activate boronic acid and aldehyde C-H bond simultaneously, triggering the synthesis of ketones through intramolecular migration. This practical and scalable method provides a straightforward approach for ketone synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Maciej Skrodzki, Victor Ortega Garrido, Aurelio G. Csaky, Piotr Pawluc
Summary: This study reports a stable cobalt(II) complex that exhibits high catalytic activity and selectivity in hydrosilylation reactions, with unprecedented tolerance towards tertiary silanes. The catalytic system shows high regioselectivity for a variety of alkynes, resulting in the formation of alpha-vinylsilanes.
JOURNAL OF CATALYSIS
(2022)
Review
Chemistry, Medicinal
Francisco Sanchez-Sancho, Marcos Escolano, Daniel Gavina, Aurelio G. Csaky, Maria Sanchez-Rosello, Santiago Diaz-Oltra, Carlos del Pozo
Summary: The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is growing due to their biological relevance. The classical approach to reach these structures is the Biginelli reaction, but it has limitations in product diversity. In this manuscript, two main strategies to overcome these limitations are discussed: modification of the reaction components and postmodification of the products. The modification of the keto ester counterpart is the most popular approach, and the use of Biginelli adducts for further modification is also highlighted.
Meeting Abstract
Radiology, Nuclear Medicine & Medical Imaging
Markus Laube, Silvia Roscales, Jens Pietzsch, Aurelio Csaky
NUCLEAR MEDICINE AND BIOLOGY
(2021)
Review
Chemistry, Multidisciplinary
Silvia Roscales, Aurelio G. Csaky
CHEMICAL SOCIETY REVIEWS
(2020)
