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Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

ABSTRACT: A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium ? ? ? ? ? allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

SUBMITTER: McCammant MS 

PROVIDER: S-EPMC3688275 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

McCammant Matthew S MS   Liao Longyan L   Sigman Matthew S MS  

Journal of the American Chemical Society 20130312 11

A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core. ...[more]

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