Reactivity and selectivity in hydrovinylation of strained alkenes.
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.
Liu
Wang
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Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States.
RajanBabu
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D000475:Alkenes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009532:Nickel