Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

• Alafia A. Ansari,
• Y. Suman Reddy and
• Yashwant D. Vankar

Beilstein J. Org. Chem. 2014, 10, 300–306, doi:10.3762/bjoc.10.27

• Alafia A. Ansari Y. Suman Reddy Yashwant D. Vankar Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India 10.3762/bjoc.10.27 Abstract A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields

• -glycosides; carbon-Ferrier rearrangement; ceric ammonium nitrate; 2-deoxy-2-aminoglycosides; Overman rearrangement; Introduction The growing significance of C-glycosides can be attributed to their potential use as inhibitors of carbohydrate-processing enzymes [1][2][3], their extraordinary stability

• -pseudoglycals are also important as the double bond can also be easily functionalized in a variety of ways. Although there is an abundance of methods reporting on the carbon-Ferrier rearrangement of glycals [9], efforts are ongoing for improvements in terms of efficiency, selectivity, time and yields of