title: Dual chiral, dual supramolecular diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to amylose scaffold.
abstract: 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 gamma-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.
authors.affiliation: Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp
authors.forename: Gaku
authors.initials: G
authors.lastname: Fukuhara
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Nakamura
authors.forename: Cheng
authors.initials: C
authors.lastname: Yang
authors.forename: Tadashi
authors.initials: T
authors.lastname: Mori
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Inoue
mesh_terms: D000688:Amylose / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D047408:gamma-Cyclodextrins; D000688:Amylose; C023792:gamma-cyclodextrin