Iron(III)-promoted aza-Prins-cyclization: direct synthesis of six-membered azacycles.
Org Lett
; 8(17): 3837-40, 2006 Aug 17.
Article
em En
| MEDLINE
| ID: mdl-16898830
ABSTRACT
[reaction see text] A new iron(III) halide-promoted aza-Prins cyclization between gamma,delta-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of gamma-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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MEDLINE
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En
Ano de publicação:
2006
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Article