Practical palladium-mediated deprotective method of allyloxycarbonyl in aqueous media

Article abstract of DOI:10.1016/S0040-4020(01)80771-7

The Allyloxycarbonyl (Alloc) moiety can be removed smoothly and selectively in good yield (73-100%) from allylic esters, carbamates and carbonates by aqueous Pd (O) catalysed allyl transfer to diethylamine in aqueous media employing a water soluble phosphine. The allyl scavenger as well as by product allyl diethylamine are volatile and easily removed in vacuo. In a two phase system an increased selectivity is seen. The method has been successfully used for deprotection of a wide range of secondary amines or base sensitive derivatives and the catalyst is efficiently recycled.