Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes

[Image: see text] The exomethylenes of 2,6-disubstituted bicyclo[3.3.1]nonan-9-ones 2 are readily isomerized over a palladium catalyst under an atmosphere of hydrogen to predominantly form the isomer 3 with C(2) symmetry with very little formation of the analogous product with C(s) symmetry. A hydro...

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Detalles Bibliográficos
Autores principales: Jung, Michael E., Lee, Gloria S., Pham, Hung V., Houk, K. N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018140/
https://www.ncbi.nlm.nih.gov/pubmed/24720691
http://dx.doi.org/10.1021/ol500710v
Descripción
Sumario:[Image: see text] The exomethylenes of 2,6-disubstituted bicyclo[3.3.1]nonan-9-ones 2 are readily isomerized over a palladium catalyst under an atmosphere of hydrogen to predominantly form the isomer 3 with C(2) symmetry with very little formation of the analogous product with C(s) symmetry. A hydrogen source is essential to effect the rearrangement.

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