SYNTHESIS AND BEHAVIOUR OF NADH MODELS BEARING A CHIRAL SULFOXIDE

Abstract

Abstract Chiral 3-sulfinyl-1,4-dihydropyridine derivatives were synthesized by asymmetric oxidation of the parent 3-pyridine sulfides with Kagan's reagent (Ti(OiPr)4/diethyl tartrate/H2O/tBuOOH = 1/2/1/1). The chemoselective oxidation conditions of the sulfur atom were optimized. One chiral NADH mimic reagent so obtained was used in the reduction of prochiral α,α',α′-trifluoroacetophenone. During this reduction a side reaction occurred i.e. desulfenylation of the reagent. The by-product was identified after trapping with methyl propiolate. This side reaction did not occur in the quinoline series.