Article
Chemistry, Medicinal
Katia Le Barbu-Debus, Anne Zehnacker
Summary: The study investigated the IR absorption and VCD spectra of a chiral amino-alcohol in DMSO-d(6) and found that the formation of intermolecular hydrogen bonds between the solute and solvent can affect the intramolecular interactions. Two solvent molecules are necessary to accurately reproduce the experimental spectra, with the first DMSO molecule capturing the main spectral modifications due to hydrogen bond formation and the second DMSO molecule being necessary for a good description of the different complexes based on their Gibbs free energy.
Article
Chemistry, Organic
Asit Ghosh, Yuriy B. Lipisa, Natalia Fridman, Alex M. Szpilman
Summary: 2-Nitrocyclopropanes with various functional groups can be obtained as single diastereoisomers in one step by introducing ketones, amides, esters, and carboxylic acids at the 1 position of corresponding unsaturated carbonyl compounds using nitromethane as the nitromethylene component. The reaction proceeds at room temperature under mild conditions and the products can be further transformed into cyclopropyl-amino acids, among others. Nitrocyclopropanes and aminocyclopropanes are important structural motifs found in biologically active compounds and natural products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinghua Wang, Shi-Jun Li, Ya-Nan Wang, Donghui Wei, Yu Lan
Summary: Desymmetrizing reactions of olefins catalyzed by N-Heterocyclic carbene (NHC) have been rapidly developing, but the origins of the chemo- and stereoselectivities in these reactions are still poorly understood. This study proposes a mechanistic map to predict how these selectivities are controlled by different active intermediates and contradicts a previous proposition regarding the determination of product structures by a transformation between a pair of isomers.
Article
Chemistry, Organic
Arnau Calbo, Rosa Griera, Joan Bosch, Mercedes Amat
Summary: Starting from racemic diastereomeric mixtures of dimethyl-2-oxocyclohexanepropionic acids (4-6), enantiopure cis-decahydroquinolines were synthesized via a dynamic kinetic asymmetric transformation and subsequent stereoselective removal of the chiral inductor. The procedure involved cyclocondensation of keto-acids 4-6 with (R)-phenylglycinol to form two major oxazoloquinolone lactams, followed by a two-step removal of the phenylglycinol moiety and reduction of the lactam carbonyl.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Adrian Lopez-Frances, Xabier del Corte, Zurine Serna-Burgos, Jesus M. de los Santos, Abel de Cozar, Javier Vicario
Summary: This study reports on the bispericyclic dimerization of cyclic molecules, where the behavior of the molecule as either diene or dienophile is determined by its location at the transition state. Additionally, a strong chiral self-recognition phenomenon is observed, and the study provides insight into the mechanism behind the high stereospecificity of the reaction through extensive DFT analysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Esther Matamoros, Mark E. Light, Pedro Cintas, Juan C. Palacios
Summary: This paper investigates the formation of Schiff bases and 1,3-oxazolidines derived from salicylaldehydes and a conformationally restricted amino alcohol. The study provides experimental evidence, including crystallographic analyses and DFT-based calculations, on imine/enamine tautomerism. The mechanistic studies reveal the prevalence of imines under thermodynamic control and the formation of 2,4-trans-oxazolidines under acylating conditions.
Article
Chemistry, Organic
Fan Wu, Zhiming Li, Chao Fu, Guan Wang, Changwu Zheng, Xiaoyu Wu
Summary: The asymmetric α-allylation of α-aryl-substituted 2-acetylimidazoles using Ni/Pd catalysts was successfully developed. The reaction involves the activation of the enolate of an acetyl imidazole by a nickel-bisoxazoline complex, followed by a reaction with a π-allylpalladium electrophile generated from an allyl alcohol derivative using a palladium-based catalyst. The broad substrate scope and the gram-scale reaction demonstrated the utility of this method.
Article
Chemistry, Inorganic & Nuclear
Yanyan Wang, Haifeng Zheng, Guoshuai Zhang, Hao Wang, Ying Xiong, Wuping Liao
Summary: Four calixarene-coordinated titanium-oxo clusters with different structures were synthesized. CIAC-258 and CIAC-261 showed excellent catalytic performance in the selective oxidation of sulfides to sulfoxides.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sushree Ranjan Sahoo, Khushboo Gupta, Vinod K. Singh
Summary: We report a chiral phosphoric acid-catalyzed enantioselective dearomative reaction that enables the synthesis of various naphthopyran derivatives from non-functionalized 1-naphthols. This method offers high yields and good enantioselectivities.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yang Gao, Phil S. Baran
Summary: A new approach to the enantiocontrolled synthesis of alpha-amino ketone derivatives is presented using a decarboxylative acylation strategy. This method yields the desired alpha-amido ketones with good yield and high enantioselectivity when an acyl chloride and an alpha-amido-containing redox-active ester are exposed to a nickel catalyst, chiral ligand, and metal reductant. The reaction has wide substrate scope, scalability, and simplifies the synthesis of known structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Amanda Bunyamin, Carol Hua, Anastasios Polyzos, Daniel L. Priebbenow
Summary: This study demonstrates the visible light induced cycloaddition reaction of singlet nucleophilic carbenes with tethered olefins, as well as additional transformations, providing a new avenue for the reactivity of nucleophilic carbenes in chemical synthesis.
Article
Chemistry, Organic
Zhanhuan Li, Hongwei Zhou, Jianfeng Xu
Summary: This study describes a rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst, producing biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields with good to excellent enantioselectivities. The formal [3 + 3] annulation reaction shows good practicality on a gram scale and the resulting cycloadduct can be further modified.
Article
Engineering, Chemical
Nicolas M. Bertero, Carlos R. Apesteguia, Alberto J. Marchi
Summary: A liquid-phase selective synthesis of 1-indanol by heterogeneous catalytic hydrogenation was reported using 1-indanone as the starting material. Cu/SiO2 catalyst showed the highest yield and selectivity, as well as high stability. Pt/SiO2 exhibited activity towards hydrogenation reactions, while Co/SiO2 showed high activity for hydrogenolysis. Physicochemical characterization and LHHW modeling were used to explain the performance of the catalysts.
CHEMICAL ENGINEERING SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Xia Zhong, Jiuqi Tan, Jianglin Qiao, Yuqiao Zhou, Cidan Lv, Zhishan Su, Shunxi Dong, Xiaoming Feng
Summary: The efficient asymmetric synthesis of a collection of small molecules with structural diversity is highly important to drug discovery. In this study, three distinct types of chiral cyclic compounds were accessible by enantioselective catalysis and sequential transformations. Experimental studies and DFT calculations were performed to probe the reaction mechanism, showing high selectivity and efficiency in the reaction of N-allenamides.
Article
Chemistry, Inorganic & Nuclear
Hiroaki Uchiyama, Dhanya Puthusseri, Jekabs Grins, Daniel Gribble, Gulaim A. Seisenbaeva, Vilas G. Pol, Vadim G. Kessler
Summary: The paper discusses the synthesis of mixed titanium-molybdenum oxides, successfully obtaining two mixed oxide products through thermal solution reduction.
INORGANIC CHEMISTRY
(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)
