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The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics 1a and 1b were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with 1a proceeded with high stereoselectivity in...
We have prepared novel NADH mimics, in which the 1,4-dihydronicotinamide structure is connected to the diacetone-D-glucose molecule via its C-1 nitrogen, e.g. compound 1a and 1b, and through the amide bond, e.g. compound 2-6, and analyzed their ability to stereoselective reduction of methyl benzoylformate. Although NADH mimics 1-3 and 6 turned out to be less effective in chirality transfer toward...
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