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

Jie Ding | Zendy; Vasumathi Desikan | Zendy; Xinxin Han | Zendy; Tom Ling Xiao | Zendy; Rongfang Ding | Zendy; William S. Jenks | Zendy; Daniel W. Armstrong | Zendy

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

Author(s) -

Jie Ding,

Vasumathi Desikan,

Xinxin Han,

Tom Ling Xiao,

Rongfang Ding,

William S. Jenks,

Daniel W. Armstrong

Publication year - 2004

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol047599i

Subject(s) - chemistry , photoisomerization , ionic liquid , isomerization , enantioselective synthesis , deprotonation , asymmetric induction , enantiomer , ionic bonding , photochemistry , ion , organic chemistry , catalysis

[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.

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