Template-assisted stereoselective photocyclodimerization of 2-anthracenecarboxylic acid by bispyridinio-appended gamma-cyclodextrin.
[reaction: see text] Four kinds of bispyridinio-appended gamma-cyclodextrin (gamma-CD) were prepared to make a molecular flask for controlling the stereoselectivity of photocyclodimerization of 2-anthracenecarboxylate. When the photocyclodimerization of 2-anthracenecarboxylate was carried out in the presence of A,E-bispyridinio-appended gamma-CD, the relative yield of one of the configurational isomers, the head-to-head/anti-isomer, was increased 1.8-fold compared to the corresponding yield in the presence of unmodified gamma-CD or in the absence of any gamma-CD. The optical yields of the photocyclodimerization reaction products also increased more than 10-fold by the addition of bispyridinio-appended gamma-CD compared with unmodified gamma-CD.
Ikeda
Hiroshi
H
Department of Bioengineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-44 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. hikeda@bio.titech.ac.jp
Nihei
Takashi
T
Ueno
Akihiko
A
D000873:Anthracenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D019281:Dimerization; D015394:Molecular Structure; D010777:Photochemistry; D011725:Pyridines / Q000737:chemistry*; D047408:gamma-Cyclodextrins / Q000737:chemistry*
D000873:Anthracenes; D002264:Carboxylic Acids; D011725:Pyridines; D047408:gamma-Cyclodextrins; C107996:anthracene-1-carboxylic acid