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.
[reaction: see text] A readily available chiral amino alcohol has been immobilized on silica by sol-gel synthesis and grafting. The solid prepared according to the latter method led to the best enantioselectivity (77% ee) described for the asymmetric addition of diethylzinc to benzaldehyde using inorganic solids.
A very active and highly enantioselective catalytic resin, designed for minimal perturbation of the catalytic center by the polymer matrix, has been assembled in two steps from (S)-triphenylethylene oxide, piperazine, and Merrifield resin and tested in the enantioselective ethylation of aldehydes. 1-Arylpropanols of 94-95% ee are obtained in high yield by the use of only 2 mol % of catalytic resin at 0 degrees C for 4 h.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.