Switchable Reactivity of Glycals Toward the Synthesis of 3-Oxo Glycals and 2-Deoxy Lactones

Abstract

The switchable reactivity of glycals has been demonstrated by the successful synthesis of 3-oxo glycals and 2-deoxy lactones directly from glycals under ambient conditions. 3-Oxo glycals were obtained from various glycals via C3-oxidation employing (NH₄)₂S₂O₈ as an oxidant in DMSO solvent at 55 °C. However, 2-deoxy lactones were synthesized through C-1 oxidation using Pd(OAc)₂ as a catalyst and K₂S₂O₈ as an oxidant in the DMSO:H₂O solvent system. The methodology is operationally simple, high-yielding, scalable, and endowed with varied substrate scope.