Studies on novel and chiral 1,4-dihydropyridines IV. Mechanistic aspects of the asymmetric reduction with chiral NADH model compounds, (S(S))-3-(p-tolylsulfinyl)-1,4-dihydropyridines

Article abstract of DOI:10.1016/S0040-4020(97)00072-0

In the reduction of ketones with NADH mimics, (S(S))-1-substituted 3-(p-tolylsulfinyl)-1,4-dihydropyridines 1, the stereospecific transfer of one of the C-4 hydrogens, which is syn to the S-O bond, was experimentally revealed to be involved by employing the 2-methyl derivative 2 and the 4-deuterated derivatives 3a and 3b. The transition state model of this reaction was also proposed by consideration of the results obtained.