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Tail‐Tied Ligands: An Immobilized Analogue of ( R )‐2‐Piperidino‐1,1,2‐triphenylethanol with Intact High Catalytic Activity and Enantioselectivity
Author(s) -
Pericàs Miquel A.,
Castellnou David,
Rodríguez Israel,
Riera Antoni,
Solà Lluís
Publication year - 2003
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.200303125
Subject(s) - chemistry , catalysis , diethylzinc , homogeneous , ligand (biochemistry) , polymer , combinatorial chemistry , stereochemistry , enantioselective synthesis , organic chemistry , biochemistry , receptor , physics , thermodynamics
A functional analogue of ( R )‐2‐piperidino‐1,1,2‐triphenylethanol was synthesized and anchored to different polymeric supports by a position remote from the active region. This strategy, leading to what we call a tail‐tied ligand, allows for the achievement of the optimal transition state geometry in the catalytic process. The catalytic activity of the resulting heterogenized ligands was investigated by online FTIR analysis. The optimum polymer was assayed in the addition reaction of diethylzinc to a large family of aldehydes rendering essentially intact high catalytic activity and enantioselectivity compared to its homogeneous counterpart.