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Synthesis of a Novel Chiral Ionic Liquid and Its Application in Enantioselective Aldol Reactions
Author(s) -
Zhou Wei,
Xu LiWen,
Qiu HuaYu,
Lai GuoQiao,
Xia ChunGu,
Jiang JianXiong
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890012
Subject(s) - cyclohexanone , aldol reaction , chemistry , enantioselective synthesis , ionic liquid , yield (engineering) , chemoselectivity , catalysis , organic chemistry , organocatalysis , materials science , metallurgy
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.