453556-43-9Relevant academic research and scientific papers
Chiral biomimetic NADH models in the benzo[b]-1,6-naphthyridine series. A novel class of stable, reactive and highly enantioselective NADH mimics
Vasse, Jean-Luc,Levacher, Vincent,Bourguignon, Jean,Dupas, Georges
, p. 4911 - 4921 (2007/10/03)
The preparation of a new class of tricyclic models 1 based on a Friedl?nder reaction between chiral piperidine-2,4-diones 2 and azomethine 3 is reported. Alkylation of the lactam allowed to install various pendant arms on the chiral cyclic inducer. The so-obtained mimics 1a,d,f,g,h,k were involved in the reduction of methyl benzoylformate to furnish methyl mandelate in 4-87% ee (R). The presence of a coordinating pendant arm proved to be essential to reach optimum results in terms of enantioinduction. Asymmetric reduction of 2-benzoylpyridine with mimics 1d,f,g produced α-phenyl-2-pyridinemethanol in 30-84% ee (R).
Influence of the C(4)-C(3)-C=O dihedral angle of chiral NADH mimics on the stereoselectivity of reductions
Vasse, Jean-Luc,Levacher, Vincent,Bourguignon, Jean,Dupas, Georges
, p. 227 - 232 (2007/10/03)
Herein we report the stereoselective synthesis of new chiral NADH mimics 2 and 13 of the benzo [b]-1,6-naphthryridine series. The synthesis of 2 and 13 relies upon a Friedlander-type condensation between the amino imine 3 and the piperidine-2,4-dione 4 bearing a stereogenic center at C(6). The resulting NADH models were involved in the reduction of methyl benzoylformate. A comparison of their performance with that of previously reported NADH mimics such as model 1, throws new light on the role played by the C(4)-C(3)-C=O dihedral angle (α) on the stereoselectivity of the hydride transfer.
