Efficient and Modular Synthesis of New Structurally Diverse Functionalized [n]Paracyclophanes by a Ring-Distortion Strategy

With the goal of synthesizing new [n]paracyclophanes, the expansion of the scope of a strategy originally disclosed by Winterfeldt et al., was investigated. This approach involves sequential Diels–Alder/retro‐Diels–Alder reactions, the applications of which have been constrained so far to steroid derivatives. An efficient access to new functionalized [9]‐, [10]‐, and [16]paracyclophanes, including original cage architectures, was developed from readily available building blocks using thermal electrocyclization and a cycloaddition/cycloreversion sequence as the key steps. Effizient, modular und einfach präsentiert sich ein Ansatz zu neuen funktionalisierten [n]Paracyclophanen mit Heteroatomen und Arylether‐, Biaryl‐ oder Lactam‐Motiven sowie Käfigarchitekturen ausgehend von leicht zugänglichen Bausteinen. Entscheidend sind dabei sequenzielle Diels‐Alder‐ und Retro‐Diels‐Alder‐Reaktionen.