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 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.
Fukuhara
Gaku
G
Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp
Nakamura
Tomohiro
T
Yang
Cheng
C
Mori
Tadashi
T
Inoue
Yoshihisa
Y
D000688:Amylose / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000737:chemistry*
D047408:gamma-Cyclodextrins; D000688:Amylose; C023792:gamma-cyclodextrin