Synthesis of Homoallylic Alcohols from Allylic Phosphates and Aldehydes with Organoaluminum Reagent Containing Al–Sn Linkage

Treatment of allylic phosphates with the reagent prepared from n-Bu3SnLi and Et2AlCl or from SnF2 and Et2AlCl affords allyltin compounds which react with aldehydes to produce homoallylic alcohols in good yields. The formation of allyltin compounds requires the catalytic amount of Pd(PPh3)4 and proceeds with inversion of the stereochemistry predominantly.