AI Article Synopsis
- - A new type of dimeric ligands called tunable heterophospholes has been created, allowing for advancements in Cu-catalyzed hydrogenation processes.
- - These ligands facilitate the simultaneous creation of two stereogenic centers in compounds like 2-substituted-1-tetralones, achieving impressive purity metrics (over 99:1 diastereomeric ratio and 98:2 enantiomeric ratio).
- - The copper ligand complexes were carefully studied using single crystal X-ray diffraction, and DFT calculations uncovered a unique transition state involving a heteroligated dimeric copper hydride.
Article Abstract
A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones dynamic kinetic resolution, simultaneously creating two contiguous stereogenic centers with up to >99 : 1 dr and 98 : 2 er. The ligand-Cu complexes were isolated and characterized by single crystal X-ray, and DFT calculations revealed a novel heteroligated dimeric copper hydride transition state.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5958347 | PMC |
| http://dx.doi.org/10.1039/c8sc00434j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Deracemization of Benzoin and its Derivatives via Kinetic, Dynamic Kinetic, Aerobic Oxidative Kinetic and Reagent-mediated resolution.
Chem Asian J
December 2024
Govt. Degree College for Men, Srikakulam, Department of Chemistry, Srikakulam, 532001, Srikakulam, INDIA.
The production of enantiomerically pure compounds remains a vital and valuable objective in modern organic chemistry due to their broad applications in fields such as biosensing, optics, electronics, photonics, catalysis, nanotechnology, and drug or DNA delivery. Optically pure α-hydroxy ketones, in particular, are key structural components in many drugs and natural products with significant biological activity. Among these, benzoin type α-hydroxy ketones, which possess two adjacent functional groups, a carbonyl and a hydroxy group, are especially important.
View Article and Find Full Text PDFAnisotropy factor spectra for weakly allowed electronic transitions in chiral ketones.
Chemphyschem
December 2024
Freie Universität Berlin: Freie Universitat Berlin, Dahlem Center of Complex Quantum Systems and Fachbereich Physik, Arnimallee 14, 14195, Berlin, GERMANY.
Quantum chemical calculations of one-photon absorption, electronic circular dichroism and anisotropy factor spectra for the A-band transition of fenchone, camphor and 3-methylcyclopentanone (3MCP) are reported. While the only weakly allowed nature of the transition leads to comparatively large anisotropies, a proper theoretical description of the absorption for such a transition requires to account for non-Condon effects. We present experimental data for the anisotropy of 3MCP in the liquid phase and show that corresponding Herzberg-Teller corrections are critical to reproduce the main experimental features.
View Article and Find Full Text PDFNovel Benzimidazole-Endowed Chalcones as α-Glucosidase and α-Amylase Inhibitors: An Insight into Structural and Computational Studies.
Molecules
November 2024
Department of PG Studies and Research in Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire 574240, Karnataka, India.
In search of novel antidiabetic agents, we synthesized a new series of chalcones with benzimidazole scaffolds by an efficient 'one-pot' nitro reductive cyclization method and evaluated their α-glucosidase and α-amylase inhibition studies. The 'one-pot' nitro reductive cyclization method offered a simple route for the preparation of benzimidazoles with excellent yield and higher purity compared to the other conventional acid- or base-catalyzed cyclization methods. H, C NMR, IR, and mass spectrum data were used to characterize the compounds.
View Article and Find Full Text PDFA New Synthesis of Enantiopure Amine Fragment: An Important Intermediate to the Anti-HIV Drug Lenacapavir.
J Org Chem
December 2024
Medicines for All Institute, Virginia Commonwealth University, Richmond, Virginia 23284-3068, United States.
Herein, we describe a new seven-step approach to prepare ()-1-(3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethan-1-amine (()-) from the inexpensive 2-(3,5-difluorophenyl)acetic acid. The key steps in the sequence include (1) the Weinreb amide-based ketone synthesis to provide an entry point to the core structure; (2) simple functional group transformations to afford the racemic amine -; and (3) dynamic kinetic resolution (DKR) to access the chiral amine ()-. This seven-step process delivered the enantiopure amine ()- in an overall isolated yield of approximately 15%.
View Article and Find Full Text PDFMethyl jasmonate enabled maintained the postharvest flavor quality of ginger (Zingiber officinale roscoe) by reducing the loss of terpene volatile compounds.
Food Chem
December 2024
Hubei key Laboratory of Spices & Horticultural Plant Germplasm Innovation & Utilization, College of Horticulture and Gardening, Yangtze University, Jingzhou 434025, Hubei, China; Spice Crops Research Institute, College of Horticulture and Gardening, Yangtze University, Jingzhou 434025, Hubei, China; College of Smart Agriculture /Institute of Special Plants, Chongqing University of Arts and Sciences, Yongchuan 402160, Chongqing, China. Electronic address:
Ginger, as a globally vital medicinal and food homologous crop, plays an irreplaceable role in human diet and healthcare. However, during the storage of ginger, the decline of physical properties and degradation of volatile flavor quality have emerged as an industrial concern that severely restricts the market value of the product. MeJA plays an essential role in extending fruit shelf life and regulate the synthesis of volatiles in horticultural products, yet its application in ginger remains unreported.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!