Nucleophilic addition of organometallic reagents to N,N-dimethyl- and SAMP-glyoxal-monohydrazones

Article abstract of DOI:10.1016/S0040-4020(98)01087-4

Nucleophilic addition of organometallics to N,N-dimethyl-glyoxal- monohydrazone occurs smoothly to give the corresponding α-hydroxy hydrazones in high yields. From these compounds, polyfunctional derivatives such as protected α-hydroxy aldehydes and α-hydroxy nitriles can be easily obtained in satisfactory to good yields. The addition to a SAMP-hydrazone proceeds with low (35% d.e.) or reasonable (60% d.e.) levels of stereoselectivity when vinylmagnesium reagents are employed.