Synthesis of allylic alcohols via organopalladium additions to unsaturated epoxides

✍ Scribed by Richard C Larock; Steven J Ilkka

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 208 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84489-5

✦ Synopsis

The reaction of aryl-and vinylpalladium compounds with vinylic and allylic epoxides provides an excellent, high yielding, regio-and stereoselective route to functionally substituted allylic alcohols which can be made catalytic in palladium. The reaction of vinylic epoxides and organolithium, -magnesium, -copper, and -boron compounds has been reported to afford allylic alcohols. Most of these reactions can accommodate little organic functionality and exhibit low regio-and/or stereoselectivity. Clean 1,Caddition is observed in the Pd(O)-catalyzed opening of vinylic epoxides by