Addition of N-benzylhydrazine to sugar δ-enlactones

Article abstract of DOI:10.1016/S0040-4020(01)85245-5

The conjugate addition - rearrangement of N-benzylhydrazine to sugar δ- enlactone with erythro configuration 1 and 2 affords mixtures of respective ribo and arabino isomers with the former one prevailing. In the case of the threo lactone 3 two regioisomers with xylo configuration are produced, whereas in the case of 4 only one isomer with the erythro configuration is formed. The stereochemical course of these reactions was explained.