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Proline‐Catalyzed Asymmetric Aldol Reaction in Guanidine‐ Derived Ionic Liquids
Author(s) -
Shah Jabbar,
Blumenthal Haiko,
Yacob Zekarias,
Liebscher Jürgen
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800111
Subject(s) - chemistry , aldol reaction , yield (engineering) , guanidine , catalysis , proline , acetone , ionic liquid , enantiomeric excess , enantiomer , enantioselective synthesis , organic chemistry , ionic bonding , ion , amino acid , biochemistry , materials science , metallurgy
Abstract A remarkable improvement of both the chemical yield (from 6% to 82%) and the enantiomeric excess (up to >99%), of ( S )‐proline catalyzed direct aldol reactions of a wide range of aldehydes with acetone was found when hexasubstituted or pentasubstituted guanidinium salts were added as ionic liquids. Effects of temperature, amount of proline and the type of guandidinium salts on the outcome of the reaction were investigated.