FeCl₂-Mediated Rearrangement of Allylic Alcohols

Authors

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

Document Type

Article

Date of Original Version

2019

Department

Chemistry

Abstract

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.

Citation/Publisher Attribution

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.