Chemoselective reactions of N1-methyl-2-hydroxy-3-methylamino-3-phenylpropanamide with electrophiles. Synthesis of chiral hexahydro-4-pyrimidones and oxazolidines

The reactivity of (2S,3S)-N1-methyl-2-hydroxy-3-methylamino-3-phenylpropanamide 1, containing three nucleophilic centres has been studied against dihaloalkanes and aldehydes. Hexahydro-4-pyrimidones or oxazolidines were obtained chemoselectively. Experimental results were explained by 'ab initio' calculations.