Osmium-Catalyzed Tethered Aminohydroxylation of Glycals: A Stereodirected Access to 2- and 3-Aminosugars

详细信息    查看全文

• 作者：Stefania Mirabella ; Francesca Cardona ; Andrea Goti
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 6, 2015
• 年：2015
• 卷：17
• 期：3
• 页码：728-731
• 全文大小：377K
• ISSN：1523-7052

文摘

The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach. Glucals and galactals showed complementary reactivity in dependence of the stage at which the reaction was performed, i.e., directly or after double-bond shift consequent to a Ferrier rearrangement (that is, on the 1,2 or 2,3-unsaturated sugar), allowing access to both classes of 2-amino (mannosamine) and 3-amino (talosamine) sugar derivatives, respectively.