It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Herein, we report a three-component Aza-Darzens reaction that generates -phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution ( vs ). This transformation constitutes a rare catalytic three-component coupling within a supramolecular assembly, providing a supramolecular solution to a synthetically challenging transformation.
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http://dx.doi.org/10.1021/jacs.9b13177 | DOI Listing |
Chemistry
February 2024
Department of Drug and Health Sciences, University of Catania, Viale Andrea Doria 6, 95125, Catania, Italy.
In recent decades, many efforts have been devoted to studying reactions catalyzed in nanoconfined spaces. The most impressive aspect of catalysis in nanoconfined spaces is that the reactivity of the molecules can be smartly driven to disobey classical behavior. A green and efficient three-component aza-Darzens (TCAD) reaction using a catalytic amount of γ-cyclodextrins (CDs) in water has been developed to synthesize N-phenylaziridines.
View Article and Find Full Text PDFInorg Chem
March 2022
Key Laboratory of Nonferrous Metal Chemistry and Resources Utilization of Gansu Province and State Key Laboratory of Applied Organic Chemistry, Key Laboratory of Special Function Materials and Structure Design, Ministry of Education, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
The exploration and development of coordination nanocages can provide an approach to control chemical reactions beyond the bounds of the flask, which has aroused great interest due to their significant applications in the field of molecular recognition, supramolecular catalysis, and molecular self-assembly. Herein, we take the advantage of a semirigid and nonsymmetric bridging ligand (H) with rich metal-chelating sites to construct an unusual and discrete 3d-4f metallacage, [ZnEr(H)(NO)Cl(HO)]·NO·CHOH·HO (). The 3d-4f cage possesses a quadruple-stranded structure, and all of the ligands wrap around an open spherical cavity within the core.
View Article and Find Full Text PDFJ Am Chem Soc
January 2020
Chemical Sciences Division, Lawrence Berkeley National Laboratory and Department of Chemistry , University of California, Berkeley , California 94720 , United States.
It has been previously demonstrated that nanovessels can be highly competent catalysts providing high rate accelerations and unique selectivity to the organic transformations which they mediate. However, for supramolecular assemblies to be considered a standard reagent in organic synthesis they must first demonstrate the ability to catalyze increasingly complex transformations. Herein, we report a three-component Aza-Darzens reaction that generates -phenylaziridines, catalyzed by a supramolecular host, that provides the stereoisomer opposite to the one generated in bulk solution ( vs ).
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!