Synthesis of polycyclic ?-lactams. Evolution of tertiary radicals generated by Cp2TiCl from 1,5- and 1,6-epoxynitriles

Synthesis of polycyclic ?-lactams. Evolution of tertiary radicals generated by Cp2TiCl from 1,5- and 1,6-epoxynitriles

Radical cyclisation induced by Cp2TiCl of several 1,5- and 1,6-epoxynitriles derived from [beta]-lactams gave 3-oxo-4-methyl-4-hydroxymethylcarbapenams or 4-oxo-5-methylbenzocarbacephems. Apart from these polycyclic [beta]-lactams, the generated alkyl tertiary radicals also evolved to enamides throu...

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Veröffentlicht in:Tetrahedron 2012-12, Vol.68 (52), p.10794-10805
Hauptverfasser: Monlen, Laura M., Grande, Manuel, Anaya, Josefa
Format: Artikel
Sprache:eng
Schlagworte:
Evolution
Radicals
Reduction
Synthesis
Tetrahedrons
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Zusammenfassung:Radical cyclisation induced by Cp2TiCl of several 1,5- and 1,6-epoxynitriles derived from [beta]-lactams gave 3-oxo-4-methyl-4-hydroxymethylcarbapenams or 4-oxo-5-methylbenzocarbacephems. Apart from these polycyclic [beta]-lactams, the generated alkyl tertiary radicals also evolved to enamides through [beta]-fragmentation and reduction and the tertiary homobenzyl radicals gave a 3,4-trans-6-hydroxymonolactam by hydrogen transfer.
ISSN:0040-4020
DOI:10.1016/j.tet.2011.11.015