Immobilization of chiral ligands on polymer fibers by electron beam induced grafting and applications in enantioselective catalysis

S Degni; C E Wilén; R Leino

doi:10.1021/ol016212y

Immobilization of chiral ligands on polymer fibers by electron beam induced grafting and applications in enantioselective catalysis

Org Lett. 2001 Aug 9;3(16):2551-4. doi: 10.1021/ol016212y.

Authors

S Degni¹, C E Wilén, R Leino

Affiliation

¹ Laboratory of Polymer Technology, Abo Akademi University, FIN-20500 Abo, Finland.

PMID: 11483058
DOI: 10.1021/ol016212y

Abstract

[reaction: see text] Styrenic TADDOL and L-prolinol-derived monomers were immobilized on polyethylene fibers by electron beam induced preirradiation grafting using styrene as comonomer. The polymer-supported chiral ligands were utilized as catalysts in the asymmetric addition of diethylzinc to benzaldehyde. Fiber-bound titanium TADDOLate gave a quantitative conversion of benzaldehyde to 1-phenylpropan-1-ol in a 97:3 S/R enantiomeric ratio. The catalyst was successfully regenerated and employed in subsequent reactions with retention of high enantioselectivities.