Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by gamma-cyclodextrins with a flexible or rigid cap.
[reaction: see text] A series of modified gamma-cyclodextrins (CDs) with a flexible or rigid cap, synthesized and used as chiral supramolecular hosts for mediating the enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid, significantly improved the chemical and optical yields of chiral head-to-head cyclodimer 3, while the gamma-CD with a rigid cap dramatically inverted the stereochemical outcomes and further improved the enantioselectivities of both head-to-tail and head-to-head dimers 2 and 3.
Yang
Cheng
C
ICORP Entropy Control Project, JST, Toyonaka, Japan.
Nakamura
Asao
A
Wada
Takehiko
T
Inoue
Yoshihisa
Y
D000873:Anthracenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D019281:Dimerization; D008958:Models, Molecular; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
D000873:Anthracenes; D002264:Carboxylic Acids; D047408:gamma-Cyclodextrins; C107996:anthracene-1-carboxylic acid