Stereospecific anti S(E)2 ' fluorination of allenylsilanes: synthesis of enantioenriched propargylic fluorides

The electrophilic fluorodesilylation of enantioenriched allenylsilanes proceeds with efficient transfer of chirality. The silylation - fluorination of propargylic alcohols occurs with overall retention of stereochemistry, a result consistent with a stereospecific anti S(E)2' mechanism for the fluorination step.