Use of the Allyloxycarbonyl Protective Group in Carbohydrate Chemistry

Abstract

Abstract Selective allyloxycarbonylation of primary hydroxyl groups was achieved by using allyl chloroformate as reagent. The allyl-oxycarbonyl group was removed selectively in the presence of the allyl protective group with the catalysts Pd(POS3)4 or RhCl-(Pφ3)3. Isomerisation of the allyl ether in the presence of the allyloxycarbonyl ester could be accomplished, albeit not completely selective, using [Ir(COD)(PMeφ2)2]PF6- Furthermore, the prop-2-enylidene dioxolane acetal was inert towards Pd(Pφ3)4 or RhCl(Pφ3)3 but was completely removed by PdCl2.