Synthesis and reactivity of nitro sugar-derived silyl nitronates

✍ Scribed by Olivier R. Martin; Faiza E. Khamis; S. Prahlada Rao

• Book ID: 104244441
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 211 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93326-x

✦ Synopsis

Silyl nitronates are readily generated from carbohydrates containing a nitromethyl group; these nitronates participate in F--catalyzed nitroaldol reactions with aldehydes provided that the nucleophilic carbon atom is sufficiently remote from the cyclic carbohydrate moiety.