Conjugate addition reactions of a (diethoxyphosphinoyl)difluoromethyl anion equivalent to acyclic and cyclic vinyl sulfones

✍ Scribed by K. Blades; D. Lapôtre; J.M. Percy

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 203 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01313-0

✦ Synopsis

Cerium-mediated conjugate additions of (diethoxyphosphinoyl)difluoromethyllithium to cyclic vinyl sulfones proceeded smoothly; reduction afforded the products of formal alkylation, attaching the difluoromethylene phosphonate group to a secondary carbon atom. With acyclic vinyl sulfones, the addition was considerably less efficient and deprotonation competed with addition. Addition failed completely in the absence of cerium(llI) chloride.