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Prolinamide‐Derived Ionic‐Liquid‐Supported Organocatalyst for Asymmetric Mono‐ and Bis‐Aldol Reactions in the Presence of Water
Author(s) -
Kucherenko Aleksander S.,
Gerasimchuk Vasiliy V.,
Lisnyak Vladislav G.,
Nelyubina Yulia V.,
Zlotin Sergei G.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500775
Subject(s) - aldol reaction , chemistry , enantioselective synthesis , ionic liquid , catalysis , adduct , aqueous solution , aqueous medium , organic chemistry , organocatalysis , ionic bonding , ion
A novel recyclable prolinamide‐derived ionic‐liquid‐supported organocatalyst of asymmetric cross‐aldol reactions in aqueous medium has been developed. In its presence, aromatic aldehydes react with cyclic or linear ketones to afford chiral aldol adducts in moderate to high yields and with excellent dr ( anti / syn up to 96:4) and ee (81–99 %) values that do not tend to decline over ten recycles of the catalyst. Furthermore, it allows a highly enantioselective catalytic synthesis of linear bis‐aldols in aqueous medium.