Date of Original Version
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 FeCl2. 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.
Oppong-Quaicoe, A. A. & DeBoef, B. (2019). FeCl2-Mediated Rearrangement of Allylic Alcohols. ACS Omega, 4(3), 6077-6083. doi: 10.1021/acsomega.9b00163
Available at: https://doi.org/10.1021/acsomega.9b00163
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.