165333-64-2Relevant academic research and scientific papers
Chiral NADH models with restricted or blocked rotation at the amide function: Attempts to interpret the mechanism of the enantioselective hydrogen transfer to methyl benzoylformate
Vitry, Christiane,Bédat, Joelle,Prigent, Yann,Levacher, Vincent,Dupas, Georges,Salliot, Isabelle,Quéguiner, Guy,Bourguignon, Jean
, p. 9101 - 9108 (2007/10/03)
Various NADH models with the following characteristics were studied and compared with previously reported models: (1) use of (S)-phenylalaninol as chiral auxiliary; (2) orientation in or out of the plane of the amide carbonyl. Despite the occurrence of apparently similar characteristics, they gave very different results in the asymmetric reduction of methyl benzoylformate. A detailed NMR study was performed in order to explain the behaviour of these models.
NADH Models in the Pyrrolopyridine Series. Role of the Cyclized Structure in the Stereocontrol of Reductions
Bedat, Joelle,Levacher, Vincent,Dupas, Georges,Queguiner, Guy,Bourguignon, Jean
, p. 327 - 328 (2007/10/02)
The synthesis of a chiral NADH model in pyrrolopyridine series is described and the asymmetric reduction of methyl benzoylformate is studied.Its asymmetric behavior compared with a cyclized analogue in naphthyridine series suggest that the orientation of the carbonyl group of the lactam plays an important role in the stereochemical control of the reduction.
