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Carbonyl Orientation Determines Regio- and Enantioselectivity in 1,2-/1,4-Reduction of an NAD Model Compound

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journal contribution
posted on 19.08.2004, 00:00 by Yuji Mikata, Shiho Aida, Shigenobu Yano
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.