Allylic 1,2- and 1,3-hydroxy phenyl sulfones undergo regioselective and diastereoselective desulfonylation with double bond migration upon treatment with [Sm(H2O)n]I2. Selectivity in these reactions is thought to arise from the formation of a chelated organosamarium intermediate followed by intramolecular protonation by samarium-bound water, which is supported by observed diastereoselectivity and stereospecificity trends along with deuterium labeling experiments. The reaction was then featured in the synthesis of the phenolic fragment of the thailandamide natural products.
Ahmad Muhamad Mustain NasohaAshfiya Nur AtqiyaAzzahra AzzahraVina Aulia Nur PratamaErvina Eka Saputri
Demas Chandra PermanaRadinald FerdiansyahFayza Putri SafiraZayid Thoriq Ali GumilangAriya Jembar PangestuRama Wijaya Abdul Rozak