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Ionic‐Liquid‐Supported Organocatalyst: Efficient and Recyclable Ionic‐Liquid‐Anchored Proline for Asymmetric Aldol Reaction
Author(s) -
Miao Weishi,
Chan Tak Hang
Publication year - 2006
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.200606059
Subject(s) - chemistry , aldol reaction , ionic liquid , acetone , proline , catalysis , organocatalysis , organic chemistry , enantioselective synthesis , hydroxyproline , combinatorial chemistry , amino acid , biochemistry
Ionic‐liquid‐anchored ( 2S,4R )‐4‐hydroxyproline 12 catalyzes direct asymmetric aldol reactions with comparable enantioselectivities in DMSO, and with superior enantioselectivities in neat acetone or 2‐butanone, than ( S )‐proline ( 8) (up to 28 % ee difference) itself. Furthermore, the supported catalyst 12 can be easily recycled and reused for at least four times without significant loss of yields and enantioselectivity.