Lewis acid mediated allylation of 2-alkanoyl-1,4-quinones with allylsilane and allylstannane

✍ Scribed by Yoshinori Naruta; Hidemitsu Uno; Kazuhiro Maruyama

• Book ID: 104243581
• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 232 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92464-5

✦ Synopsis

Allyltrimethybtane

reacts with 2-alkamyl-1,4-quirwnes regioselectively to afford conjugate addition products which can be derived to 2-alkanoyl-3-allylhydroquinone diacetate, while alZyltriphenylsilane reacts tith the quinone to give naphthofman.

Recently regioselective allylation of quinones with allylstannane was developed,2 and successfully applied to the synthesis of naturally occurring isoprenylquinones (e.g. ubiquinones, plastoquinones, menaquinones, and phylloquinones).3