THE CONVERSION OF VINYL TRIFLATES INTO GAMMA'-HYDROXY-ALPHA,BETA-ENONES

Vinyl triflates have been converted into gamma'-hydroxy-alpha,beta-eno nes through their palladium-catalysed coupling with 1-butyn-4-ols foll owed by the reaction of the obtained 1-hydroxy-3-yn-5-enes in an acidi c CH2Cl2/3 N HCl two-phase system in the presence of the n-BuN4Cl/PdCl 2 combination. Both the coupling step and the conversion of the carbon -carbon triple bond into the ketonic group have been performed at room temperature. The conversion of vinyl triflates into gamma'-hydroxy-al pha,beta-enones can be carried out through a one-flask process, withou t the isolation of 1-hydroxy-3-yn-5-enes.