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FeCl(2)-Mediated Rearrangement of Allylic Alcohols

[Image: see text] 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 m...

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Detalles Bibliográficos
Autores principales: Oppong-Quaicoe, Anita A., DeBoef, Brenton
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648291/
https://www.ncbi.nlm.nih.gov/pubmed/31459755
http://dx.doi.org/10.1021/acsomega.9b00163
Descripción
Sumario:[Image: see text] 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.