Org. Lett., 7 (2), 335 -337, 2005. 10.1021/ol047599i S1523-7060(04)07599-6
Web Release Date: December 22, 2004

Copyright © 2004 American Chemical Society

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

Jie Ding, Vasumathi Desikan, Xinxin Han, Tom L. Xiao, Rongfang Ding, William S. Jenks, and Daniel W. Armstrong*

Chemistry Department, Iowa State University, Ames, Iowa 50011

sec4dwa@iastate.edu

Received November 22, 2004

Abstract:

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--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.

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