Open AccessReceptors functionalized with chiral aza‐crown ether rings. Attempted enantioselective catalysis of a Michael addition reaction
Author(s) -
Schuurman Ruud J. W.,
Grimbergen Reinier F. P.,
Scheeren Hans W.,
Nolte Roeland J. M.
Publication year - 1996
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19961150704
Subject(s) - enantioselective synthesis , enantiopure drug , catalysis , crown ether , michael reaction , chemistry , ether , stereochemistry , combinatorial chemistry , organic chemistry , ion
A series of receptors functionalized with chiral aza‐crown ether rings was synthesized. These compounds were studied as enantiopure catalysts for the addition of benzenethiols to cyclohex‐2‐en‐1‐one. Binding of 4‐hydroxybenzenethiol in these molecules allows for the orientation of the thiol with respect to an asymmetric catalytic site. This orientation was, however, found to be counterproductive for enantioselective catalysis.
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