Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses

alpha-2-Deoxyglycosides were successfully synthesized by means of microwave-assisted glycosylation. Hex-1-en-3-uloses were treated with a catalytic amount of AlCl3 and various O-nucleophiles including alcohols and sugars under microwave conditions. The desired alpha-2-deoxy-ulosides products were obtained in good to excellent yields with high stereoselectivity (alpha/beta >= 88/12). Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.