Abstract

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 0103-5053.  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.