The facile synthesis of the stabilized axial and equatorial conformers of spiro-β-lactams was achieved via entrapment of cyclohexanone imines (Schiff bases) with acetoxyacetyl chloride in a [2 + 2]-cycloaddition reaction followed by their kinetic resolution. The immobilization of the racemic substrates on an inert solid support significantly reduced the reaction time and improved the enantioselectivity of conformers during kinetic resolution. The mechanism of the formation of the spiro-β-lactams was explored using B3LYP/6-31+G* level quantum chemical calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo200363x | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Coarse-Graining Chemical Networks by Trimming to Preserve Energy Dissipation.
J Phys Chem Lett
January 2025
Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
Continuous production of entropy and the corresponding energy dissipation is a defining characteristic of nonequilibrium systems. When a system's full chemical kinetic description is known, its entropy production rate can be computed from the microscopic rate constants. However, such a calculation typically underestimates energy dissipation when the states of the underlying system are mesoscopic, i.
View Article and Find Full Text PDFCorrection: Magin et al. Impact of Non-Covalent Interactions of Chiral Linked Systems in Solution on Photoinduced Electron Transfer Efficiency. 2023, , 9296.
Int J Mol Sci
January 2025
Voevodsky Institute of Chemical Kinetics and Combustion, 630090 Novosibirsk, Russia.
The journal's Editorial Office and Editorial Board are jointly issuing a resolution and removal of the Journal Notice linked to this article [...
View Article and Find Full Text PDFA High-Resolution Crystallographic Study of Cytochrome c6: Structural Basis for Electron Transfer in Cyanobacterial Photosynthesis.
Int J Mol Sci
January 2025
College of Chemistry and Life Science, Beijing University of Technology, Beijing 100124, China.
Cyanobacterial cytochrome c6 (Cyt c6) is crucial for electron transfer between the cytochrome b6f complex and photosystem I (PSI), playing a key role in photosynthesis and enhancing adaptation to extreme environments. This study investigates the high-resolution crystal structures of Cyt c6 from PCC 7942 and PCC 6803, focusing on its dimerization mechanisms and functional implications for photosynthesis. Cyt c6 was expressed in using a dual-plasmid co-expression system and characterized in both oxidized and reduced states.
View Article and Find Full Text PDFCrystallisation Based Deracemisation and Chiral Resolution of Small Molecules.
Chem Asian J
January 2025
Mahatma Gandhi University, School of Chemical Sciences, Priyadarsini Hills, 686560, Kottayam, INDIA.
Enantiomeric separation of chiral molecules is pivotal for exploring fundamental questions about life's origin and many other fields. Crystallisation is an important platform for the separation of chiral molecules, elegantly applied to many systems, for instance, the formation of conglomerates, where the enantiomers crystallise as separate phases. Many approaches have been proposed to explore crystallisation-driven enantiomeric separation with fewer insights into the complex pathways associated with the separation processes.
View Article and Find Full Text PDFDynamic Kinetic Resolution-Based Asymmetric Transfer Hydrogenation of Racemic 2-Substituted Quinolines.
J Am Chem Soc
January 2025
Faculty of Pharmaceutical Sciences, Shenzhen University of Advanced Technology, Shenzhen 518107, China.
The synthesis of chiral tetrahydroquinolines (THQs) has garnered significant interest from medicinal chemists due to their frequent presence as pharmacophores in bioactive compounds. While existing synthetic methods have primarily focused on THQs with single or multiple endocyclic chiral centers, the selective construction of THQs with both and cyclic chiral centers remains a significant challenge that requires further development. This study introduces a dynamic kinetic resolution (DKR)-based transfer hydrogenation of racemic 2-substituted quinolines, which yields structurally novel chiral THQs with consecutive and cyclic chiral centers in excellent yields and stereoselectivities (59 examples, with generally >20:1 dr and >90% ee, up to three consecutive stereocenters).
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!