Tetrahedron p. 733 - 740 (1989)
Update date:2022-08-12
Topics:
Zehani, Sadek
Lin, Jian
Gelbard, Georges
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 monosaccharide-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 Mg2+ catalysis is discussed and the possibility of using others Lewis acids - especially chiral ones - is examined.
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