Chiral β-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations

Article abstract of DOI:10.1016/S0040-4020(98)00317-2

Enantiomerically pure u and l β-amino sulfoxides have been easily obtained from the respective homochiral α-amino alcohols. The absolute configuration at the created stereogenic centre was assigned by CD spectra and by X-ray analysis. Conformational analysis of the title compounds was carried out using quantum chemical energy-geometry optimization. Thus established conformational behavior explained the strongly configuration dependent NMR spectral patterns observed for the u and l diastereomers.