Premium
Broadening the Synthetic Scope of the Iron(III)‐Catalyzed Aza‐Prins Cyclization
Author(s) -
Carballo Rubén M.,
Valdomir Guillermo,
Purino Martín,
Martín Víctor S.,
Padrón Juan I.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901372
Subject(s) - chemistry , tosyl , prins reaction , reactivity (psychology) , derivatization , sulfonyl , alkyl , ring (chemistry) , medicinal chemistry , organic chemistry , stereochemistry , catalysis , high performance liquid chromatography , medicine , alternative medicine , pathology
The nature and influence of the N ‐sulfonyl group in aza‐Prins cyclization and the reactivity of the six‐membered aza‐cycle generated has been studied. The aza‐Prins cyclization of γ,δ‐unsaturated amines with a tosyl group at the nitrogen atom produces 2‐alkyl‐4‐halo‐1‐tosyl‐1,2,5,6‐tetrahydropyridines with a halovinyl function, extraordinarily stable to further derivatization and detosylation conditions. To modulate the reactivity of such aza‐cycles, a general study of the aza‐Prins cyclization reaction was performed with several sulfonamides. Ring formation occurs satisfactorily with both N ‐nosyl and N ‐mesylamines providing optimal conditions for further synthetic transformations. To exemplify the scope of this methodology, a short synthesis of the alkaloid coniine was successfully carried out.