[reaction: see text] Employing zeolite as the reaction medium, it is possible to change the enantio (from achiral dienones) and diastereo (from chiral dienones) selectivities during the oxa-di-pi-methane rearrangement of 2,4-cyclohexadienones.
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http://dx.doi.org/10.1021/ol010245w | DOI Listing |
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Oncogenomics, Institute of Biopharmaceutics and Health Engineering, Tsinghua Shenzhen International Graduate School, Shenzhen 518055, China.
The high percentage of sp-hybridized carbons and the presence of chiral carbon centers could contribute to increased molecular complexity, enhancing the likelihood of clinical success of drug candidates. Three-dimensional (3D) bridged motifs have recently garnered significant interest in medicinal chemistry. Bicyclo[2.
View Article and Find Full Text PDFOrg Lett
December 2024
Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Jinan University, Guangzhou 510632, Guangdong, China.
This paper describes an iridium-catalyzed allylation of ring-fused pyrazolones that proceeds with excellent regio-, diastereo- and enantio-selectivities. The approach exploits unactivated, racemic allylic alcohols as a source of allyl building blocks. Asymmetric syntheses of a series of biologically relevant, chiral pyrazolones highlight the utility of the methodology.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Chemistry Department, Ben-Gurion University of the Negev, Campus st. 1, Beer Sheva, 8410501, Israel.
Recent attempts to mimic enzyme catalysis using simple, short peptides have been successful in enhancing various reactions, but the on-demand, temporal or spatial regulation of such processes by external triggers remains a great challenge. Light irradiation is an ideal trigger for regulating molecular functionality, since it can be precisely manipulated in time and space, and because most reaction mediums do not react to light. We herein report the selection of a photo-switchable amphiphilic peptide catalyst from a small library of isomeric peptides, each containing an azobenzene-based light responsive group and a catalytic histidine residue.
View Article and Find Full Text PDFChem Sci
August 2024
Department of Chemistry, National Demonstration Centre for Experimental Chemistry Education, Yanbian University Yanji 133002 People's Republic of China
An important subject of porous organic materials is their capacity to access enantioselectivity due to their high surface area, controllable pore size, and ease of functionalization. However, recyclability of enantio-separation is a challenge, mainly due to the complex procedures of recovery and refreshing from enantiomers. For the first time, we combined nanochannel technology and supramolecular chiral assembly to achieve efficient enantioselectivity.
View Article and Find Full Text PDFAnal Chem
August 2024
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
This work presents a novel strategy for postmodifying probes using dynamic covalent chemistry. Leveraging reversible interactions between boronic acid and diols, we obtained a panel of F-labeled probes with distinct resolving abilities. This approach enables rapid identification of probes with satisfactory performance, streamlining synthesis, and enhancing efficiency in chiral analysis.
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