Shiho Aida

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An optically active, axially chiral NAD model compound(1) with a quinoline ring system was reduced by the chiral NADH model compound (4), affording a mixture of 1,2- and 1,4-dihydroquinolines. The carbonyl orientation governs the molecular arrangement in the transition state of the reaction and determines the regio- and enantioselectivity of the product.
The regio- and enantioselectivity of the reduction of an NAD model compound having axial chirality with respect to the C(3)(quinolinium)-C(carbonyl) bond, 3-piperidinylcarbonyl-1,2,4-trimethylquinolinium ion (1), by using several reducing agents is described. Reaction of 1 with sodium hydrosulfite affords the 1,4-reduced product,(More)
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