Hydroxylamine derivatives as nucleophiles in Ferrier glycosylation: synthesis of aminoxy pseudoglycals

Abstract

The use of hydroxylamine derivatives as the aminoxy equivalent nucleophiles in Ferrier glycosylation catalyzed by various acid catalysts is described. The reaction of tri-O-protected D-glucal with N-hydroxyphthalimide or N-hydroxysuccinimide was effectively promoted by a catalytic amount of zinc(II) chloride to produce the corresponding aminoxy pseudoglycal in good yields and preferential anomeric selectivity.