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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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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 |
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. |
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