Work

FeCl2-Mediated Rearrangement of Allylic Alcohols

Year: 2019

Type: article

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.

Source: ACS Omega

DOI: 10.1021/acsomega.9b00163

Authors: Anita A. Oppong-Quaicoe, Brenton DeBoef

Institution: University of Rhode Island

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $750

Funders: National Science Foundation, Division of Chemistry