4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanones 4a-e have been reduced to optically active 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanols 5a-e with baker's yeast. We subjected the alcohols possessing (S)-configuration to Ferrier' rearrangement with tri-O-acetyl-D-glucal 6 which furnished new unsaturated O-glycosides 7a-e. The crystallographic data of the glycosides 7b confirmed the (S)-configuration for the aglycone portion of the carbon atom.

Uma fácil e eficiente síntese para obtenção de beta-aminocetonas 5a, 6 e gama-aminoálcoois 1a, 2a, 3, 4 enantiomericamente puros a partir de L-prolinol 7 e L-prolina 15 é descrita. A etapa principal da reação foi o uso do reagente de Tebbe que permitiu a transformação da função éster a um enol éter que após hidrólise formou a cetona sem nenhuma racemização.

An easy and efficient route for the synthesis of enantiomerically pure beta-aminoketones 5a, 6 and gamma-aminoalcohols 1a, 2a, 3, 4 from L-prolinol 7 and L-proline 15 is described. One of the key steps is the use of Tebbe's reagent allowing the transformation of the ester function to an enol ether without any racemization.