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Abstract
New chiral 2-(4-substituted-piperidino)-3-vinylpyridines undergo stereoselective isomerization to pyrido [1,2- a][1,8]naphthyridines. The stereoselectivity of this reaction was found dependent on the experimental conditions (temperature and solvent polarity) and the stereoelectronic features of the piperidino substituent. NMR spectroscopy allowed the determination of the compound conformation in solution and the relative configuration of the cyclized products. A mechanistic approximation to the diastereoselectivity based on molecular mechanics is put forward.
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