Stereoselectivity of hydrogen transfer with chiral NADH models as a function of configuration and conformation

…, J Duflos, G Dupas, J Bourguignon, G Quéguiner

Index: Combret, Yves; Torche, Jean-Jacques; Ple, Nelly; Duflos, Jack; Dupas, Georges; Bourguignon, Jean; Queguiner, Guy Tetrahedron, 1991 , vol. 47, # 45 p. 9369 - 9382

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Citation Number: 23

Abstract

NADH model compounds bearing chiral amide groups have been synthesized. One of these models, 3, possessed the 1, 6-naphtyridinone structure and the key step of its synthesis was a cross coupling reaction which was optimized on the basis of consideration of the mechanism. In this bicyclic model 3, the amide carbonyl dipole is forced in a transoid orientation. In model 1, the free rotation around the C-3-C O amide bond is not hindered ...