Stereospecific addition of formaldehyde dialkylhydrazones to sugar aldehydes. Synthesis of cyanohydrins and α-hydroxy aldehydes

Article abstract of DOI:10.1016/0040-4039(96)01226-9

Formaldehyde dialkylhydrazones smoothly add to sugar aldehydes without any need of promoter or catalyst. α-Hydroxy dialkylhydrazones, which are obtained in good yields and high stereoselectivities, have been successfully transformed in cyanohydrins by treatment with magnesium monoperoxyphtalate (MMPP) and in O-protected α-hydroxy aldehydes by ozonolysis or HCl mediated hydrolysis. No racemization was observed in the cleavage of the dialkylhydrazone group.