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A Solid‐Supported Organocatalyst for Continuous‐Flow Enantioselective Aldol Reactions
Author(s) -
Ayats Carles,
Henseler Andrea H.,
Pericàs Miquel A.
Publication year - 2012
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201100570
Subject(s) - aldol reaction , chemistry , catalysis , enantioselective synthesis , flow chemistry , filtration (mathematics) , continuous flow , polystyrene , adduct , derivative (finance) , organic chemistry , chemical engineering , polymer , statistics , physics , mathematics , mechanics , engineering , financial economics , economics
Asymmetric aldol reactions catalyzed by a novel polystyrene‐immobilized proline derivative occur in short reaction times with excellent diastereo‐ and enantioselectivity. The catalyst can be recovered by simple filtration and shows very high reusability. The high activity depicted by the supported catalyst and its chemical and mechanical stability have allowed its application in packed‐bed reactors for continuous flow processing. This system can produce enantio‐ and diastereomerically pure aldol adducts under continuous flow conditions with a residence time of 26 min. Furthermore, the reactor allowed processing of four different aldol products in sequence without any decrease in both catalytic activity and optical purity. The effective catalyst loading could be reduced to 1.6 % (six‐fold reduction of catalyst loading compared to the corresponding batch process).