Dual Chiral, Dual Supramolecular Diastereodifferentiating Photocyclodimerization of 2-Anthracenecarboxylate Tethered to Amylose Scaffold

Newly synthesized 6-O-(2-anthroyl)amylose (AC-Am; 51% substitution) was photolyzed in (aqueous) DMSO solutions to give HH dimers as major products (after saponification), with modest enantiomeric excesses (ee) of 12−15% and 1−2% for syn-HT and anti-HH dimers, respectively. Addition of γ-cyclodextrin switched the product selectivity to HT and enhanced the ee of syn-HT up to 37%, while the chiral sense of anti-HH was inverted by changing the irradiation temperature, demonstrating usefulness of the dual-supramolecular approach to photochirogenesis.