Chemoselective acylation of some oxidofunctionalised organolithium compounds

✍ Scribed by Miguel Yus; Joaquı́n Gomis

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 110 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)00758-0

✦ Synopsis

Once oxidofunctionalised organolithium compounds 1 (easily prepared by reductive ring opening of isochroman and phthalan by DTBB-catalysed lithiation) were transmetallated with ZnBr 2 /CuCN•2LiCl and reacted successively with a carboxylic acid anhydride and an acyl chloride in THF at 08C, the corresponding differently acylated compounds 4 were obtained after hydrolysis with water. The anhydride performed the O-acylation exclusively and the acyl chloride carried out the C-acylation.