THE SYNTHESIS OF E-ENOL ETHERS OF PROTECTED 4-AMINO ALDEHYDES

The title compounds, a novel class of protected homoallylic amines, ha ve been synthesised by a short and efficient route. Acrolein acetals w ere converted by a modified Michaelis-Arbuzov reaction into alpha-alko xyallyl(diphenyl)phosphine oxides. 1,3-Dipolar cycloaddition to the al kene part of these molecules gave 5-diphenylphosphinoyl-4,5-dihydroiso xazoles, which were reductively cleaved to obtain delta-amino-beta-hyd roxy-alpha-alkoxyalkyl (diphenyl)phosphine oxides. After selective pro tection as the N-acetyl derivatives, stereospecific Wittig-Horner diph enylphosphinic acid elimination gave the title compounds.