Tetradehydro-Diels–Alder Reactions of Flexible Arylalkynes via Folding Inside a Molecular Cage

Authors:
Publisher website
Google Scholar
Abstract
The tetradehydro-Diels-Alder (TDDA) reaction is a useful transformation for the rapid assembly of polycyclic scaffolds from simple linear precursors in a single synthetic step. However, the reaction requires careful substrate design and harsh reaction conditions to overcome the inherent entropic cost for this transformation. Herein we report an efficient site-selective TDDA transformation within a self-assembled Pd6L4 cage. Despite the large size, the flexibility of the employed substrates allows for efficient encapsulation within the host cavity. The rate of thermal cyclization of the encapsulated guest was found to be greatly enhanced, and high product selectivity for an unsymmetrical substrate was observed. The efficiency of this system relies on the precise conformational control of the substrate within the confined space of the host cage.
Funding Information
  • Japan Society for the Promotion of Science (19H05461, 21K14641, 23H01783, P22338)

This publication has 24 references indexed in Scilit: