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

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• 作者：Hao-Yuan Wang ; Christopher J. Simmons ; Yu Zhang ; Angela M. Smits ; Paul G. Balzer ; Shuojin Wang ; Weiping Tang
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：508-511
• 全文大小：489K
• ISSN：1523-7052

文摘

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.