Use of Chiral Ionic Liquids as Solvents for the Enantioselective Photoisomerization of Dibenzobicyclo[2.2.2]octatrienes

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-π-methane rearrangement. Results indicate t...

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Bibliographic Details
Published in:Organic letters 2005-01, Vol.7 (2), p.335-337
Main Authors: Ding, Jie, Desikan, Vasumathi, Han, Xinxin, Xiao, Tom L, Ding, Rongfang, Jenks, William S, Armstrong, Daniel W
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Benzene Derivatives - chemistry
Cyclization
Ions
Molecular Structure
Photochemistry
Polycyclic Aromatic Hydrocarbons - chemistry
Solvents - chemistry
Stereoisomerism
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Summary: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-π-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol047599i