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Synthesis of a Novel Chiral Ionic Liquid and Its Application in Enantioselective Aldol Reactions

✍ Scribed by Wei Zhou; Li-Wen Xu; Hua-Yu Qiu; Guo-Qiao Lai; Chun-Gu Xia; Jian-Xiong Jiang

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
241 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A novel chiral ionic liquid, compound 1, based on camphorsulfonic acid, was prepared. A catalytic amount of 1 readily promotes L‐proline‐catalyzed aldol reactions, with good chemoselectivity, both in H~2~O and in organic solvents. Further, the aldol reaction of cyclohexanone with 4‐nitrobenzaldehyde afforded 2‐[hydroxy(4‐nitrophenyl)methyl]cyclohexanone (6) in 98% yield with high enantioselectivity (94% ee) when large amounts of 1 (5 equiv.) were used as promoter.

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