Synthesis of Tertiary Alcohols via the Use of the Allyldimethylsilyl Moiety as a Latent Hydroxyl Group in the Kumada-Fleming-Tamao Reaction

Article abstract of DOI:10.1016/0040-4039(91)80521-7

The phenyldimethylsilyl to hydroxyl transformation fails in the cases where a cyclic tertiary carbon center is involved as was observed in the synthesis of phorbol C-ring models.An alternate functionality in the form of allyldimethylsilane (ADMS) is found to work well in these and other cases involving tertiary centers.With proper choice of reagents, the ADMS group can be employed as a latent alcohol in systems containing ketones, esters, arenes, and vinyl groups.