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Re(2)O(7)-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles

Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the a...

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Detalles Bibliográficos
Autores principales: Sittiwong, Wantanee, Richardson, Michael W, Schiaffo, Charles E, Fisher, Thomas J, Dussault, Patrick H
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740507/
https://www.ncbi.nlm.nih.gov/pubmed/23946852
http://dx.doi.org/10.3762/bjoc.9.174
Descripción
Sumario:Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the acetal dimers. Aldehydes react under similar conditions to furnish good yields of dithioacetals. Reactions of hemiacetals with nitrogen nucleophiles are unsuccessful. 1,2-Dioxolan-3-ols (peroxyhemiacetals) undergo Re(VII)-promoted etherification but not allylation. Hydroperoxyacetals (1-alkoxyhydroperoxides) undergo selective exchange of the alkoxide group in the presence of either Re(2)O(7) or a Brønsted acid.