Chiral Catalyst-Directed Dynamic Kinetic Diastereoselective Acylation of Anomeric Hydroxyl Groups and a Controlled Reduction of the Glycosyl Ester Products

• DOI: 10.1021/acs.orglett.6b03683
• Publication Date: 2017-01-12T18:56:39Z
• Authors: Hao-Yuan Wang; Christopher J. Si...; Yu Zhang; Angela M. Smits; Paul G. Balzer; Shuojin Wang; Weiping Tang
• Keywords: 01 natural sciences; 0104 chemical sciences

A catalytic method is developed for the diastereoselective acylation of the anomeric hydroxyl group in diverse carbohydrates to form either α- or β-anomeric esters. While exclusive formation of the β-isomer was observed in most sugar substrates with one enantiomer of the chiral catalyst, moderate to high α-selectivity was obtained by using the other enantiomer of the chiral catalyst. The resulting α- and β-anomeric esters have very different reactivity toward a reduction reaction.