Chiral NADH Models in the Pyrido[3,2-c]azepin Series. Conformational Effect of the Carbonyl Group in the Stereocontrol of Reductions
1996; Oxford University Press; Volume: 25; Issue: 5 Linguagem: Inglês
10.1246/cl.1996.359
ISSN1348-0715
AutoresJoëlle Bédat, Vincent Levacher, Georges Dupas, G. QUEGUINER, Jean Bourguignon,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoAbstract 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.
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