The Allyloxycarbonyl (Alloc) moiety can be removed smoothly and selectively in good yield (73-100%) from allylic eaters, carbamates and carbonates by aqueous Pd (0) catalyzed 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.
Véronique Michaud, Yves Leterrier, Adrien Julien Demongeot
Christian Ludwig, Rudolf Paul Wilhelm Jozef Struis, Ajay Bhagwan Patil, Viktoria Paetzel