We describe herein the direct organocatalytic asymmetric nucleophilic substitution reaction of 2-benzylfurfurals with benzyl alcohols and allylic alcohol in the absence of any metal catalysts and ligands. A series of γ-regioselective products were obtained in high yields and up to 99% enantiomeric excess.
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http://dx.doi.org/10.1021/acs.joc.4c02937 | DOI Listing |
Chemistry
March 2025
Organic Chemistry I, Saarland University, Campus C4.2, D-, 66123, Saarbrücken.
Deprotonated trimethylsilylethanol is an excellent nucleophile for Matteson homologations. It can be introduced in high yields and the products are stable under the usual basic reaction conditions. After two further homologation steps, the protective group is automatically cleaved off via a six-membered ring O-B coordination, providing highly substituted tetrahydrofurans.
View Article and Find Full Text PDFAcc Chem Res
March 2025
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599 United States.
ConspectusAromatic functionalization reactions are some of the most fundamental transformations in organic chemistry and have been a mainstay of chemical synthesis for over a century. Reactions such as electrophilic and nucleophilic aromatic substitution (EAS and SAr, respectively) represent the two most fundamental reaction classes for arene elaboration and still today typify the most utilized methods for aromatic functionalization. Despite the reliable reactivity accessed by these venerable transformations, the chemical space that can be accessed by EAS and SAr reactions is inherently limited due to the electronic requirements of the substrate.
View Article and Find Full Text PDFACS Appl Mater Interfaces
March 2025
School of Electrical Engineering, Ben-Gurion University of the Negev, Beer-Sheva 8410501, Israel.
There is an urgent need today for interface management with recognition layers composed of short receptor molecules, with excellent specificity and affinity toward a target molecule, for a wide range of sensing applications. The current work demonstrates a specific detection of a G-type nerve agent, which is based on a nucleophilic substitution reaction between the surface-bound 4-amino-2-((dimethylamino)methyl)phenol (amino-2-DMAMP) receptors and the diethyl chlorophosphate (DCP) simulant. The specificity and affinity of 2-DMAMP toward DCP are demonstrated with P-nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS/MS).
View Article and Find Full Text PDFOrg Lett
March 2025
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India.
Naturally occurring protoalkaloids, such as colchicine and colchicoside, have significant medical applications and are used globally to treat a variety of diseases. We report herein a C(sp)-N(sp) bond formation protocol via a TfO (triflic anhydride)-assisted one-pot aromatic nucleophilic substitution (SAr) reaction on various naturally occurring biologically active compounds such as colchicine, 3-demethyl colchicine, and 2-methoxy tropone under mild reaction conditions. Synthesis of bench-stable heterotropone quaternary salts was achieved by the reaction of tropolone alkaloids with diverse non-nucleophilic -heterocycles.
View Article and Find Full Text PDFACS Chem Neurosci
March 2025
Department of Chemistry, University of Missouri, Columbia, Missouri 65211, United States.
Glutamate is an important excitatory neurotransmitter, while GABA is an inhibitory neurotransmitter. However, direct and accurate visualization of these important signaling agents by a chemical sensor is still very challenging. Here, a novel coumarin-based fluorescent sensor for the selective labeling and imaging of amino acids in neurons has been developed.
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