Article
Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes
Author/s | Puigcerver, Julio
Marín Luna, Marta Iglesias Sigüenza, Francisco Javier Alajarin, Mateo Martinez-Cuezva, Alberto Berna, Jose |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2024-01-24 |
Deposit Date | 2024-06-24 |
Published in |
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Abstract | Herein we describe an effective transmission of chirality, from mechanically planar chirality to point chirality, in hydrogen-bonded [2]rotaxanes. A highly selective mono-N-methylation of one (out of four) amide N atom at ... Herein we describe an effective transmission of chirality, from mechanically planar chirality to point chirality, in hydrogen-bonded [2]rotaxanes. A highly selective mono-N-methylation of one (out of four) amide N atom at the macrocyclic counterpart of starting achiral rotaxanes generates mechanically planar chirality. Followed by chiral resolution, both enantiomers were subjected to a base-promoted intramolecular cyclization, where their interlocked threads were transformed into new lactam moieties. As a matter of fact, the mechanically planar chiral information was effectively transferred to the resulting stereocenters (covalent chirality) of the newly formed heterocycles. Upon removing the entwined macrocycle, the final lactams were obtained with high enantiopurity. |
Funding agencies | Ministerio de Ciencia e Innovación (MICIN). España Agencia Estatal de Investigación. España Fundación Séneca-CARM, Murcia, España. |
Project ID. | PID2019-106358GB-C22
PID2020-113686GB Fundación Séneca-CARM 21907/PI/22 |
Citation | Puigcerver, J., Marín Luna, M., Iglesias Sigüenza, F.J., Alajarin, M., Martinez-Cuezva, A. y Berna, J. (2024). Mechanically Planar-to-Point Chirality Transmission in [2]Rotaxanes. Journal of the American Chemical Society, 146 (5), 2882-2887. https://doi.org/10.1021/jacs.3c11611. |
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