γ-Regioselective reaction of metaloxysilyl-substituted allyllithium derived from allyldiphenylsilanol

Article abstract of DOI:10.1016/S0040-4039(97)01124-6

Treatment of allyldiphenylsilanol (1) with two equivalents of butyllithium in the presence of HMPA at -45°C afforded silylallyllithium 2a bearing an oxide anion on the silicon atom. The reaction of 2a with various electrophiles gave γ-products selectively in good yields. Higher regio- and stereoselectivities were achieved in the reaction of silyl-substituted allyllithium derived from potassium allylsilanolate with butyllithium.