Use of chiral ionic liquids as solvents for the enantioselective photoisomerization of dibenzobicyclo[2.2.2]octatrienes.
[Reaction: see text] Six chiral ionic liquids were prepared and evaluated as "chiral induction solvents" in which two different dibenzobicyclo[2.2.2]octatrienes were photoisomerized to chiral products. Enantiomeric excesses from 3 to 12% were obtained from the photochemical di-pi-methane rearrangement. Results indicate that the chiral induction derives from an ion pairing interaction of the deprotonated diacids with the ionic liquid cation. This is the first report on chiral induction via a chiral IL for an irreversible, unimolecular photochemical isomerization.
Ding
Jie
J
Chemistry Department, Iowa State University, Ames, Iowa 50011, USA.
Desikan
Vasumathi
V
Han
Xinxin
X
Xiao
Tom L
TL
Ding
Rongfang
R
Jenks
William S
WS
Armstrong
Daniel W
DW
D000475:Alkenes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D003500:Cyclization; D007477:Ions; D015394:Molecular Structure; D010777:Photochemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D001555:Benzene Derivatives; D007477:Ions; D011084:Polycyclic Aromatic Hydrocarbons; D012997:Solvents