Unknown

Dataset Information

0

Palladium hydride promoted stereoselective isomerization of unactivated di(exo)methylenes to endocyclic dienes.

ABSTRACT: 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 C2 symmetry with very little formation of the analogous product with C(s) symmetry. A hydrogen source is essential to effect the rearrangement.

SUBMITTER: Jung ME 

PROVIDER: S-EPMC4018140 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Palladium hydride promoted stereoselective isomerization of unactivated di(exo)methylenes to endocyclic dienes.

Jung Michael E ME   Lee Gloria S GS   Pham Hung V HV   Houk K N KN  

Organic letters 20140411 9

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 C2 symmetry with very little formation of the analogous product with C(s) symmetry. A hydrogen source is essential to effect the rearrangement. ...[more]

Similar Datasets

Unknown π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions.
| S-EPMC6467781 | biostudies-literature
Unknown Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.
| S-EPMC2732350 | biostudies-literature
Unknown Asymmetric hydrovinylation of unactivated linear 1,3-dienes.
| S-EPMC2836389 | biostudies-literature
Unknown Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp<sup>3</sup>)-H bonds with acetonitrile.
| S-EPMC5477045 | biostudies-literature
Unknown Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.
| S-EPMC5778876 | biostudies-literature
Unknown Palladium-catalysed alkene chain-running isomerization.
| S-EPMC5705238 | biostudies-literature
Unknown Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.
| S-EPMC7328341 | biostudies-literature
Unknown Synthesis of (1<i>E</i>,3<i>E</i>)-1,4-diarylbuta-1,3-dienes promoted by μ-OMs palladium-dimer complex.
| S-EPMC6661770 | biostudies-literature
Unknown Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic ?-Hydrogen Elimination.
| S-EPMC4497606 | biostudies-literature
Unknown Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.
| S-EPMC3129978 | biostudies-literature