Synthesis of trans-perhydroisoquinolines by 6- endo- trig radical cyclization of amino-tethered vinyl bromides and cyclohexenes

Bu 3SnH-promoted cyclization of several N-(2-bromoprop-2-enyl)- N-[(4-oxocyclohex-1-enyl)methyl]alkylamines is reported. It has been found that the generated vinyl radicals evolve through a 6- endo-cyclization pathway giving rise to the corresponding 4,6-functionalized perhydroisoquinolines in a pre...

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Bibliographic Details
Published in:Tetrahedron 2007-02, Vol.63 (6), p.1372-1379
Main Authors: Quirante, Josefina, Vila, Xavier, Paloma, Laura, Guiu, Josep M., Bonjoch, Josep
Format: Article
Language:English
Subjects:
Decahydroisoquinolines
Nitrogen heterocycles
Radical cyclization
Vinyl radicals
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Summary:Bu 3SnH-promoted cyclization of several N-(2-bromoprop-2-enyl)- N-[(4-oxocyclohex-1-enyl)methyl]alkylamines is reported. It has been found that the generated vinyl radicals evolve through a 6- endo-cyclization pathway giving rise to the corresponding 4,6-functionalized perhydroisoquinolines in a prevalent trans-relative configuration. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.11.087