Diastereoselective guest-shape dependent [2+2]-photodimerization of 2-cyclopenten-1-one trapped within a metal-organic framework

UV-induced [2+2] dimerization of 2-cyclopenten-1-one and 2-methyl-2-cyclopenten-1-one was successfully carried out in a single-crystal-to-single-crystal manner within a porous metal-organic framework. Intermolecular contacts direct the orientation of the & alpha;,& beta;-enone molecules within the host channels, which drives the subsequent photoaddition reaction in a facile and diastereoselective fashion, yielding head-to-tail anti dimers only.

Automated summary

UV-induced [2+2] dimerization of 2-cyclopenten-1-one and 2-methyl-2-cyclopenten-1-one was successfully carried out in a single-crystal-to-single-crystal manner within a porous metal-organic framework. Interactions among molecules dictate the positioning of α,β-enone molecules within the host channels, facilitating subsequent photoaddition reaction and yielding exclusive head-to-tail anti dimers.