1,2-Disubstituted Planar Chiral Ferrocene Derivatives from Sulfonamide-Directed ortho-Lithiation: Synthesis, Absolute Configuration, and Chiroptical Properties
| Autor: | Ravutsov, M., Dobrikov, G. M., Dangalov, M., Nikolova, R., Dimitrov, V., Mazzeo, G., Longhi, G., Abbate, S., Paoloni, L., Fuse, M., Barone, V., Fuse', Marco |
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| Přispěvatelé: | Ravutsov, M., Dobrikov, G. M., Dangalov, M., Nikolova, R., Dimitrov, V., Mazzeo, G., Longhi, G., Abbate, S., Paoloni, L., Fuse', M., Barone, V. |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Organic Chemistry Absolute configuration 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Sulfonamide Inorganic Chemistry Planar chemistry Ferrocene derivatives Physical and Theoretical Chemistry Settore CHIM/02 - Chimica Fisica |
| Popis: | A straightforward approach to the synthesis of a series of 1,2-disubstituted planar chiral ferrocenes was achieved using the ortho-directed lithiation of chiral ferrocenesulfonamides followed by a reaction with electrophilic reactants. The planar 1,2-functionalized ferrocenesulfonamides were obtained in good yields, and the individual diastereoisomers could be isolated in the pure form. The relative configurations of the chemical groups in positions 1 and 2, which are relevant for the planar chirality, were derived from NMR experiments, and the absolute configuration was determined by X-ray crystallography. Experimental ECD and VCD spectra were recorded, assigned, and interpreted by means of state-of-the-art quantum chemical computations, which allow for an unbiased analysis of the different structural factors that tune the overall spectroscopic features. A straightforward approach to the synthesis of a series of 1,2-disubstituted planar chiral ferrocenes was achieved using the ortho-directed lithiation of chiral ferrocenesulfonamides followed by a reaction with electrophilic reactants. The planar 1,2-functionalized ferrocenesulfonamides were obtained in good yields, and the individual diastereoisomers could be isolated in the pure form. The relative configurations of the chemical groups in positions 1 and 2, which are relevant for the planar chirality, were derived from NMR experiments, and the absolute configuration was determined by X-ray crystallography. Experimental ECD and VCD spectra were recorded, assigned, and interpreted by means of state-of-the-art quantum chemical computations, which allow for an unbiased analysis of the different structural factors that tune the overall spectroscopic features. |
| Databáze: | OpenAIRE |
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