| Autor: |
Puigcerver J; Departamento de Quimica Organica, Facultad de Quimica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, E-30100 Murcia, Spain., Marin-Luna M; Departamento de Quimica Organica, Facultad de Quimica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, E-30100 Murcia, Spain., Iglesias-Sigüenza J; Departamento de Quimica Organica and Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Universidad de Sevilla, E-41012 Sevilla, Spain., Alajarin M; Departamento de Quimica Organica, Facultad de Quimica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, E-30100 Murcia, Spain., Martinez-Cuezva A; Departamento de Quimica Organica, Facultad de Quimica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, E-30100 Murcia, Spain., Berna J; Departamento de Quimica Organica, Facultad de Quimica, Regional Campus of International Excellence 'Campus Mare Nostrum', Universidad de Murcia, E-30100 Murcia, Spain. |
| Abstrakt: |
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. |
