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Browsing Artículos by browse.metadata.advisor "Berna, José"

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    Effects on Rotational Dynamics of Azo and Hydrazodicarboxamide-Based Rotaxanes
    (Multidisciplinary Digital Publishing Institute, 2017-06-28) Saura Sanmartín, Adrián; Martinez-Espin, Juan S.; Martinez-Cuezva, Alberto; Alajarín, Mateo; Berna, José; Berna, José; Química Orgánica
    The synthesis of novel hydrogen-bonded [2]rotaxanes having two pyridine rings in the macrocycle and azo- and hydrazodicarboxamide-based templates decorated with four cyclohexyl groups is described. The different affinity of the binding sites for the benzylic amide macrocycle and the formation of programmed non-covalent interactions between the interlocked components have an important effect on the dynamic behavior of these compounds. Having this in mind, the chemical interconversion between the azo and hydrazo forms of the [2]rotaxane was investigated to provide a chemically-driven interlocked system enable to switch its circumrotation rate as a function of the oxidation level of the binding site. Different structural modifications were carried out to further functionalize the nitrogen of the pyridine rings, including oxidation, alkylation or protonation reactions, affording interlocked azo-derivatives whose rotation dynamics were also analyzed.
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    Ring-to-thread chirality transfer in [2]rotaxanes for the synthesis of enantioenriched lactams
    (Wiley-VCH, 2022-09-19) Lopez-Leonardo, Carmen; Saura Sanmartín, Adrián; Marin-Luna, Marta; Alajarín, Mateo; Martinez-Cuezva, Alberto; Berna, Jose; Martinez-Cuezva, Alberto; Berna, José; Química Orgánica
    The synthesis of chiral mechanically interlocked molecules has attracted a lot of attention in the last few years, with applications in different fields, such as asymmetric catalysis or sensing. Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows enantioenriched value-added compounds, such as lactams of different ring sizes and amino acids, to be obtained. The chiral information is effectively transmitted across the mechanical bond from the encircling ring to the interlocked lactam. High levels of enantioselectivity and full control of the regioselectivity of the final cyclic compounds are attained.