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Science  01 Mar 2002:
Vol. 295, Issue 5560, pp. 1605
DOI: 10.1126/science.295.5560.1605b

In olefin metathesis, two unsaturated organic molecules exchange substituent groups that are attached to carbon-carbon double bonds (an example is the reaction of 2-butene and ethylene to produce propylene). Metathesis can be an efficient synthetic route, and increasingly sophisticated catalysts are providing access to targets that would otherwise be difficult to prepare. However, most metathesis catalysts are homogeneous and hence difficult to remove from the reaction. For practicality in a commercial context, supported catalysts would be preferable.

Based on their previously reported homogeneous chiral metathesis catalyst, prepared in situ from commercially available components, Hultzsch et al. have developed a polymer-supported version, which retains appreciable reactivity and excellent enantioselectivity in asymmetric olefin metathesis reactions. The slightly lower activity may result from less efficient diffusion of substrate molecules to the catalyst. The product contains less residual metal and can be isolated by filtration and solvent evaporation; furthermore, the supported catalyst can be recycled, although efficiency drops after a few cycles. Chiral metathesis catalysts of this kind are of particular interest for combinatorial synthesis and medicinal chemistry. — JU

Angew. Chem. Int. Ed.41, 589 (2002).

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