A series of diastereomerically pure aminophosphine oxides derived from pyridine- 3-carboxaldehyde and chiral amine was synthesized. The aminophosphine oxides were obtained by an addition reaction of the diphenylphosphine oxide or racemic t-butylphenylphosphine oxide to the optically active, corresponding chiral aldimines, which were obtained from pyridine-3-carboxaldehyde and enantiomers of alfa-methyl benzyl - amine. The formed diastereomers were easy separated by crystallization from acetone.
Resolution-enhanced H NMR spectra of six single diastereomers of fused-ring sulfur-containing lactams have been recorded and interpreted. In joint analysis of derived couplings Ť/HH> performed with use of the Karplus-Conroy type relationship and results of static MM calculations, it was possible to determine the configuration of title compounds and the conformation elucidation of their six-membered rings. Simultaneously, the stereochemistry of the observed ring-closure reaction was determined. The application of TNDO/2 method for the prediction of n JHH values is also briefly discussed.
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