期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 1, 页码 281-289出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo052037d
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资金
- NIGMS NIH HHS [GM-67187] Funding Source: Medline
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.
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