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

✍ Scribed by Vanda Cerè; Francesca Peri; Salvatore Pollicino; Alfredo Ricci

• Book ID: 104209031
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 761 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01087-4

✦ Synopsis

Nucleophilic addition of organometallics to N,N-dimethyl-glyoxal-monohydrazone occurs smoothly to give the corresponding a-hydroxy hydrazones in high yields. From these compounds, polyfunctional derivatives such as protected a-hydroxy aldehydes and a-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.c.) levels of stereoselectivity when vinylmagnesium reagents are employed.