Sodium Iodide/tert‐Butyl(dimethyl)silyl Chloride‐Induced Isomerization of 2,3‐Allenols to 2(E)‐Enals

Abstract

Through an unexpected C=C bond migration, 2(E)-enals were efficiently prepared highly stereoselectively in moderate to good yields via the sodium iodide/tert-butylA C H T U N G T R E N N U N G (dimethyl)silyl chloride (NaI/ TBSCl)-mediated reaction of the easily available 2,3allenols. Based on a careful mechanistic study, including control experiments and deuterium-labeling experiments, an electron-withdrawing substituent group in the 4 position has been proven to be crucial and a possible mechanism has been proposed.