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Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.
Acc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFPalladium-catalysed asymmetric cascade transformations of 4-alken-2-ynyl carbonates to construct complex frameworks.
Chem Sci
December 2024
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University Chengdu 610041 China +86 28 85502609.
As a class of readily available and multifunctional building blocks, the chemistry of 4-alken-2-ynyl carbonates remains to be explored. Presented herein is a palladium-catalysed cascade transformative reaction between 4-alken-2-ynyl carbonates and -functionalised activated alkenes. Achiral 1,1-bisalkyl-4-alken-2-ynyl carbonates undergo highly regioselective propargylic substitution with -hydroxyphenyl-tethered activated alkenes, and an auto-tandem vinylogous addition, unusual central-carbon Tsuji-Trost alkylation, protonation and β-H elimination process is followed to furnish fused and spirocyclic frameworks with high structural complexity.
View Article and Find Full Text PDFStereoselective 1,1'-glycosylation reactivity tuning with protecting groups.
Org Biomol Chem
January 2025
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, Vienna, A-1190 Austria.
Chemical 1,1'-glycosylation for the synthesis of non-reducing disaccharides is complicated by the need to simultaneously control the stereochemistry at two anomeric centers. While considerable progress has been made in the synthesis of α,α-disaccharides, the assembly of 1,1'-β,β- and 1,1'-β,α-linked non-reducing sugars has received comparatively less attention. Many naturally occurring non-reducing disaccharides and their biologically active mimetics feature asymmetrically located functional groups at different positions on the two pyranose rings, highlighting the demand for reliable stereoselective methods to synthesize fully orthogonally protected 1,1'-conjugated sugars suitable for targeted functionalisation to create important biomolecules.
View Article and Find Full Text PDFSynthesis of Enantiopure - and -Fused Octahydroisoindole-1-Phosphonic Acids from Octahydroisoindolones.
J Org Chem
January 2025
Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001, 62209 Cuernavaca, Morelos, Mexico.
Phosphonic analogs of octahydroisoindole-1-carboxylic acids are bicyclic proline derivatives of interest in drug design and enzymatic mechanism studies. Here we report the stereoselective synthesis of the - and -fused octahydroisoindole system using oxazoloisoindolone lactam and 1,2-cyclohexanedicarboxylic anhydride as advanced chiral precursors, respectively, yielding enantiopure octahydroisoindolone intermediates with the desired stereochemistry at the ring junction. Finally, using these intermediates, the target (1,3a,7a)- and (1,3a,7a)-octahydroisoindole-1-phosphonic acids and their enantiomers were obtained with complete stereocontrol via highly diastereoselective addition of trimethyl phosphite to chiral -acyliminium ions as the key step.
View Article and Find Full Text PDFNeighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2- Stereoselectivity in Nucleophilic Substitution Reactions of Furanosyl Acetals.
J Org Chem
January 2025
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
Nucleophilic substitution reactions of C-2-acyloxy furanosyl acetals can be highly diastereoselective. We here show that the presence of a less electron-donating -nitrobenzoyloxy group at C-2 of a furanosyl acetal can be of use to control the 1,2- stereoselectivity of acetal substitution reactions with higher stereoselectivity than the analogue with the more electron-donating benzoyloxy group, just as what was observed in the pyranosyl system. Computational results support a reaction manifold involving both open oxocarbenium ions and -dioxolenium ions to provide the 1,2- and 1,2- products.
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