Preparation of aromatic geraniol analogues via a Cu(I)-mediated Grignard coupling

Abstract

Difunctional allylic terpenes are important synthetic building blocks. Functionalization of protected geranyl derivatives by SeO2/t-BuO2H adsorbed on SiO2 provides a convenient route to such compounds. The chosen protecting groups clearly influence the oxidation process. Also, an efficient synthesis of 2-geranylphenol derivatives via a Cu(I)-mediated Grignard coupling of 2-lithiophenols and geranyl substrates was developed.

Keywords

• allylic oxidation
• selenium dioxide
• homoallylic alcohols
• Grignard coupling
• 2-geranylphenols