Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes

Three complementary strategies have been explored to obtain stereodefined 1,3 diols starting from easily accessible syn β-hydroxy acylsilanes: fluoride induced migrations of substituents on silicon, a Grignard addition followed by protodesilylation and Tischenko-type reactions. Preliminary data on scope and limitations of these processes are presented.