The Pd-catalyzed allyl-allyl cross-coupling between allyl electrophiles and allylboron nucleophiles is documented. Branched 1,5-dienes are formed in good yields, with enantioselectivity up to 99:1 er. The current method overcomes previous limitations, including the use of electron-poor substrates and the ability to differentiate the product olefins in subsequent transformations. The catalyst can also be recycled for the subsequent one-pot Suzuki coupling procedure.

Synthesis of chiral branched 1,5-dienes containing β-vinylboronic ester via Pd-catalyzed allyl-allyl cross-coupling

244th National Meeting (2012)

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