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Polymer-bound bis(oxazoline) as a chiral catalyst

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TETRAHEDRON-ASYMMETRY
卷 12, 期 10, 页码 1475-1478

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(01)00245-2

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A chiral bis(oxazoline) was grafted on ArgoGel and used in the palladium-catalysed substitution of (+/-)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate. The enantioselectivity was the same as that observed when the analogous monomeric catalyst was used (94-95% e.e.), despite the fact that the C-2 symmetry of the ligand was affected when coupled to the polymer. The polymer-supported catalyst could be recycled several times after removal of precipitated Pd(0). The polymer-bound bis(oxazoline) was also applied in a zinc-catalysed Diels-Alder reaction but lower selectivity and reactivity than the monomer was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.

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