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Use of Chiral Ionic Liquids as Solvents for the Enantioselective Photoisomerization of Dibenzobicyclo[2.2.2]octatrienes
Organic Letters
  • Jie Ding, Iowa State University
  • Vasumathi Desikan, Iowa State University
  • Xinxin Han, Iowa State University
  • Tom L. Xiao, Iowa State University
  • Rongfang Ding, Iowa State University
  • William S. Jenks, Iowa State University
  • Daniel W. Armstrong, Iowa State University
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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.

Reprinted (adapted) with permission from Organic Letters, 7(2); 335-337. Doi: 10.1021/ol047599i. Copyright 2005 American Chemical Society.

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American Chemical Society
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Jie Ding, Vasumathi Desikan, Xinxin Han, Tom L. Xiao, et al.. "Use of Chiral Ionic Liquids as Solvents for the Enantioselective Photoisomerization of Dibenzobicyclo[2.2.2]octatrienes" Organic Letters Vol. 7 Iss. 2 (2004) p. 335 - 337
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