Regio- and stereochemistry on the electrophilic trapping of allylic samariums generated by reductive cleavage of allylic ethers with (C5Me5)2Sm(thf)n

Bond fission of the C-O bond of allylic benzyl ethers with Cp*2Sm(thf)n produced samarium complexes in good yields. Ease of cleavage was observed to be comparable to the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio- and stereochemistry on the electrophilic trappings of the allylic complexes produced were dependent on the type of electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to produce blanched homoallylic alcohols with anti-diastereoselectivity.