Abstract
Hantzsch esters 3 and 4 have been used as NADH models instead of the well documented nicotinamides 1 for the sake of greater flexibility in the preparation and chemical modifications. Compounds 3 and 4 , bearing monosaocharide-derived substituents in the 4- or in both the 3- and 5-positions were examined in the asymmetric reduction of several prochiral ketones: namely methyl phenylglyoxylate, trifluoroacetophenone and 2-acetyl pyridine. The e.e. 's obtained are discussed in terms of the structure of the sugar residue and its position on the dihydropyridine ring. The effects of Mg 2+ catalysis is discussed and the possibility of using others Lewis acids - especially chiral ones - is examined.
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