391899-85-7Relevant academic research and scientific papers
Chiral NAHD models in the pyrido[3,2-c]azepin series. Conformational effect of the carbonyl group in the stereocontrol of reductions
Bedat, Joelle,Levacher, Vincent,Dupas, Georges,Queguiner, Guy,Bourguignon, Jean
, p. 359 - 360 (1996)
Asymmetric reduction of methyl benzoylformate with the chiral NADH model 2 in the pyrido[3,2-c]azepin series afforded methyl mandelate in 91% optical yield. The high enantioselectivity observed with model 2 is compared with cyclized analogues 1a and 1b in the naphthyridine and pyrrolo[3,4-b]pyridine series respectively. The stereochimical outcome of the reaction is discussed in relation to the out-of-plane orientation of the amide group with respect to the dihydropyridine ring in the transition state.
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.
