One-pot deoxygenative conversion of a ribonucleoside to enaminonucleosides involving 1,2-hydride shift rearrangement

Article abstract of DOI:10.1016/0040-4020(96)00159-7

5'-O-Trityl-3'-O-mesyluridine on reaction with secondary amines produced 1-(2,3-dideoxy- 2-N-dialkylamino-5-O-trityl- D-glycero--pent-2-enofuranosyl) uracil involving 1,2-hydride shift. The reaction proceeded through the formation of 2'-ketouridine in situ which was evident from the formation of both the α- and β-anomers of the enaminonucleosides.