Tetrahedron

Stable annelated chiral NADH models with a rigidified amide part in the quinoline series: synthesis, reactivity and grafting on a Merrifield resin

…, G Dupas, V Levacher, G Quéguiner, J Bourguignon

Index: Vitry, Christiane; Vasse, Jean-Luc; Dupas, Georges; Levacher, Vincent; Queguiner, Guy; Bourguignon, Jean Tetrahedron, 2001 , vol. 57, # 15 p. 3087 - 3098

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Citation Number: 41

Abstract

The synthesis of new chiral nicotinamide adenine dinucleotide hydrogenated models derived from quinoline is described. Using a biomimetic approach, the out-of-plane positioning of the amide carbonyl was obtained by involving the chiral auxiliary in a lactam structure. It is shown that electron-donating groups on the benzene ring of the quinoline structure are necessary to obtain high chemical yields during the reduction of methyl ...