allylsilane has been researched along with trifluoroacetamide* in 1 studies
1 other study(ies) available for allylsilane and trifluoroacetamide
| Article | Year |
|---|---|
Dual activation in asymmetric allylsilane addition to chiral N-acylhydrazones: method development, mechanistic studies, and elaboration of homoallylic amine adducts.
[reaction: see text] Chiral N-acylhydrazones derived from commercially available 4-benzyl-2-oxazolidinone provide a rigid, conformationally restricted template to impart facial selectivity in additions to C=N bonds. In the presence of indium(III) trifluoromethanesulfonate [In(OTf)3], N-acylhydrazones undergo highly diastereoselective fluoride-initiated additions of allylsilanes (aza-Sakurai reaction). Mechanistic studies including control experiments and comparisons with allyltributylstannane, allylmagnesium bromide, and allylindium species implicate a dual activation mechanism involving addition of an allylfluorosilicate species to a chelate formed from In(OTf)3 and the chiral N-acylhydrazone. The N-N bonds of the adducts are readily cleaved in a two-step protocol to provide synthetically useful homoallylic N-trifluoroacetamides. Further elaboration of the latter compounds through Wacker oxidation and olefin metathesis provides diversely functionalized building blocks and expands the potential applications of this C-C bond construction approach to asymmetric amine synthesis. Topics: Acetamides; Acylation; Aldehydes; Alkenes; Amines; Electrons; Fluoroacetates; Hydrazones; Ketones; Magnetic Resonance Spectroscopy; Molecular Structure; Nitrogen; Silanes; Silicon; Stereoisomerism; Trifluoroacetic Acid | 2006 |