Chemoselectivity in the conjugate addition of allylsilane to Michael acceptors

✍ Scribed by George Majetich; Ada M. Casares; D. Chapman; M. Behnke

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 229 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81803-1

✦ Synopsis

The allylic carbanion species generated by treatment of allylsilane with fluoride ion undergoes highly chemoselective conjugate addition to a series of Michael acceptors for which alternative known allylation procedures proved less general.

Conjugate addition of most nucleophilic reagents to an ~1 &-unsaturated system can be achieved routinely using an organocopper reagent or a copper-catalyzed Grignard reagent. 1 House and Fischer,2 however, observed that the condensation of allyllithium cuprate with an cl@-enone was highly substrate dependent. Their findings inspired a search for a general means of allylating a,@-unsaturated functions.