FeCl 2 -Mediated Rearrangement of Allylic Alcohols

Anita A. Oppong-Quaicoe, University of Rhode Island
Brenton Deboef, University of Rhode Island


A mild, one-pot procedure to produce 3-substituted allylic alcohols from α,β-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl 2 . The proposed mechanism indicates that a syn-facial migration occurs for the major product. Yields as high as 98% for the one-pot reaction are reported.