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Title

Iron(III)-Promoted Aza-Prins-Cyclization:  Direct Synthesis of Six-Membered Azacycles

AuthorsCarballo, Rubén M.; Ramírez, Miguel A.; Rodríguez, Matías L.; Martín, Víctor S.; Padrón, Juan I.
KeywordsHydrocarbons
Aldehydes
Inorganic compounds
Cyclization
Ions
Issue Date26-Jul-2006
PublisherAmerican Chemical Society
CitationOrganic Letters 8(17): 3837–3840 (2006)
AbstractA 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.
Publisher version (URL)https://doi.org/10.1021/ol061448t
URIhttp://hdl.handle.net/10261/212261
DOI10.1021/ol061448t
ISSN523-7060
E-ISSN1523-7052
Appears in Collections:(IPNA) Artículos
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