Selective tin and zinc mediated allylations of carbonyl compounds in aqueous media

✍ Scribed by C. Petrier; J. Einhorn; J.L. Luche

• Book ID: 104229220
• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 169 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)99068-3

✦ Synopsis

Aldehydes undergo preferentlal allyla=ion ~n the presence of ketones by che c~n or zinc mediated method, easily effected in aqueous media.

Allylacions of carbonyl compounds co homoallyllc alcohols ~s an important syn~hecic pathway 2. its hlgh potential in the build-up of some natural compounds has sc~mulaceo numerous studles and me=hods uclllzlng organometalllcs derlvea from alumlnum , boron, chromlum, tin, titanium 2 ano cerlum 3 have been developed.

We recently reported the unexpected reaction of allyllc halides wlzh aldehydes ana kezones ~n the presence of zinc in aqueous mem~a I. Homoallylic alcohols are obtained in yields of synthetic value by chls mechanistically intriguing process. Since then, we have found chat zhis reac~lon can also be efflcien~ly performed by using mecalllc ~in under sonlcaclon In a wacer-~etranydrofuran mixture to afford the rearranged homoallylic alcohol 4.