Iron(III)-Promoted Aza-Prins-Cyclization: Direct Synthesis of Six-Membered Azacycles
A new iron(III) halide-promoted aza-Prins cyclization between γ,δ-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of γ-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon−carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products.
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| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | artículo biblioteca |
| Language: | English |
| Published: |
American Chemical Society
2006-07-26
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| Subjects: | Hydrocarbons, Aldehydes, Inorganic compounds, Cyclization, Ions, |
| Online Access: | http://hdl.handle.net/10261/212261 |
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