Cargando…

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...

Descripción completa

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
_version_ 1782480031363104768
author Jung, Michael E.
Lee, Gloria S.
Pham, Hung V.
Houk, K. N.
author_facet Jung, Michael E.
Lee, Gloria S.
Pham, Hung V.
Houk, K. N.
author_sort Jung, Michael E.
collection PubMed
description [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.
format Online
Article
Text
id pubmed-4018140
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-40181402015-04-11 Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes Jung, Michael E. Lee, Gloria S. Pham, Hung V. Houk, K. N. Org Lett [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. American Chemical Society 2014-04-11 2014-05-02 /pmc/articles/PMC4018140/ /pubmed/24720691 http://dx.doi.org/10.1021/ol500710v Text en Copyright © 2014 American Chemical Society
spellingShingle Jung, Michael E.
Lee, Gloria S.
Pham, Hung V.
Houk, K. N.
Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title_full Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title_fullStr Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title_full_unstemmed Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title_short Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes
title_sort palladium hydride promoted stereoselective isomerization of unactivated di(exo)methylenes to endocyclic dienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4018140/
https://www.ncbi.nlm.nih.gov/pubmed/24720691
http://dx.doi.org/10.1021/ol500710v
work_keys_str_mv AT jungmichaele palladiumhydridepromotedstereoselectiveisomerizationofunactivateddiexomethylenestoendocyclicdienes
AT leeglorias palladiumhydridepromotedstereoselectiveisomerizationofunactivateddiexomethylenestoendocyclicdienes
AT phamhungv palladiumhydridepromotedstereoselectiveisomerizationofunactivateddiexomethylenestoendocyclicdienes
AT houkkn palladiumhydridepromotedstereoselectiveisomerizationofunactivateddiexomethylenestoendocyclicdienes