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.
Treatment of α-bromo carbonyl compounds with the reagent prepared from n-Bu3SnLi and Et2AlCl or from SnCl2 and Et2AlCl affords enolates which react with ketone or aldehyde to give β-hydroxy carbonyl compounds in good to excellent yields. The reactions proceed similarly with the reagents which are generated from R3PbLi (R=Ph, n-Bu) and Et2AlCl. Catalysis by the added Pd(PPh3)4 complex promotes the reduction effectively and improves the yields of the desired adducts. The regio- and stereoselectivities are disclosed.
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