The chalcogeno-Baylis-Hillman reaction: A new preparation of allylic alcohols from aldehydes and electron-deficient alkenes

Article abstract of DOI:10.1016/S0040-4020(98)83041-X

The chalcogeno-Baylis-Hillman reaction catalyzed by sulfides and selenides, the group 16 element compounds, in the presence of Lewis acids was developed. The reactions proceeded smoothly by the use of 1 equiv of TiCl₄ to give the coupling products in moderate to good yields. Bischalcogenides and related compounds were investigated as a catalyst, and 1,5- diselenocyclooctane gave the best result owing to stabilization of a cationic intermediate by the transannular interaction.