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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

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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]

PMID: 24720691

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