Abstract
Hantzsch esters have been chosen as models for the reducing coenzyme NADH; chirality was introduced on the dihydropyridine ring with substituents derived from protected sugars. Chiral and non-chiral Hantzsch esters were grafted onto chloromethylated polystyrene and the reducing action of the polymers thus obtained was studied using prochiral ketones. The reduction by soluble models is catalysed by magnesium, but the supported models exhibit a preferential solvation effect which hinders the action of the catalyst. The effects on reactivity and enantioselectivity are discussed.
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