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Reactivity and selectivity in hydrovinylation of strained alkenes.

ABSTRACT: The scope of Ni(II)-catalyzed hydrovinylation has been extended to strained alkenes such as heterobicyclic [2.2.1]heptanes and cylobutenes. Reactions involving the heterobicyclic compounds are rare examples for this class of compounds where the metal-catalyzed C-C bond-forming reactions proceed without a concomitant ring-opening process. While the enantioselectivity in these systems remains modest, hydrovinylation of endo-5,6--bis-benzyloxymethylbicyclo[2.2.1]hept-2-ene gives excellent yield (>90%) of the product with one of the highest enantioselectivities (95-99% ee) reported for a C-C bond-forming reaction of norbornenes.

SUBMITTER: Liu W

PROVIDER: S-EPMC3037430 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Reactivity and selectivity in hydrovinylation of strained alkenes.

Liu Wang W RajanBabu T V TV

The Journal of organic chemistry 20101021 22

The scope of Ni(II)-catalyzed hydrovinylation has been extended to strained alkenes such as heterobicyclic [2.2.1]heptanes and cylobutenes. Reactions involving the heterobicyclic compounds are rare examples for this class of compounds where the metal-catalyzed C-C bond-forming reactions proceed without a concomitant ring-opening process. While the enantioselectivity in these systems remains modest, hydrovinylation of endo-5,6--bis-benzyloxymethylbicyclo[2.2.1]hept-2-ene gives excellent yield (>9 ...[more]

PMID: 20964350

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