O-Maltosylation of Heterocyclic Ketene Aminals

The stereoselective synthesis of Ø-maltosides by reacting benzoyl-substituted heterocyclic ketene aminals 1 or 2 with acetylated maltosyl bromide 3 was investigated. Compounds 1 or 2 reacted with 3 in the presence of mercuric cyanide to give O-maltosides 4 or 5 with E-configuration. While 1 reacted with 3 in the presence of calcium hydride to give O-maltosides 6 with Z-configuration.