SYNTHESIS AND BEHAVIOR OF NADH MODELS BEARING A CHIRAL SULFOXIDE

Chiral 3-sulfinyl-l, 4-dihydropyridine derivatives were synthesized by asymmetric oxidation of the parent 3-pyridine sulfides with Kagan's reagent (Ti(OiPr)4/diethyl tartrate/H20/tBuOOH = 1/2/1/1). The che-moselective 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. © 1992, Taylor & Francis Group, LLC. All rights reserved.