Carbonyl orientation determines regio- and enantioselectivity in 1,2-/1,4-reduction of an NAD model compound.
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.
KYOUSEI Science Center, Nara Women's University, Nara 630-8506, Japan. mikata@cc.nara-wu.ac.jp
Yuji
Y
Mikata
Shiho
S
Aida
Shigenobu
S
Yano
D008956:Models, Chemical; D015394:Molecular Structure; D009243:NAD / Q000737:chemistry*; D010084:Oxidation-Reduction; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism
D011804:Quinolines; D009243:NAD