Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
PAZ, J. Luis and RODRIGUES, J. Augusto R.. Preparation of aromatic geraniol analogues via a Cu(I)-mediated Grignard coupling. J. Braz. Chem. Soc. [online]. 2003, vol.14, n.6, pp. 975-981. ISSN 1678-4790. http://dx.doi.org/10.1590/S0103-50532003000600014.
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.