A Ring Size-Selective Reduction of Lactones Using SmI_2 and H_20

摘要

The discovery of reagent systems that allow the selective manipulation of functional groups is crucial for advancements in synthesis. Of particular value are reagent systems that allow functional groups with apparently similar reactivities to be distinguished by the re-routing of transformations through less-conventional intermediates. Here we report that the reducing system SrmI_2-H_2O not only differentiates between the carbonyl groups of esters and lactones but also shows complete ring size-selectivity for six-membered lactones.