REDUCTIONS WITH NADH MODELS II: ASYMMETRIC INDUCTION WITH SUGAR SUBSTITUTED HANTZSCH ESTERS OR WITH CHIRAL LEWIS ACIDS

Article abstract of DOI:10.1016/0040-4020(89)80103-6

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.

Full text of DOI:10.1016/0040-4020(89)80103-6

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.