A homoallylpinacolboronic ester has been applied in cobalt-catalyzed Alder ene reactions with 1-phenyl-1-propyne as the model alkyne to generate Alder ene intermediates with an allyl-boronate subunit. These intermediates are converted in situ with aldehydes in an allylboration reaction. The diastereoselectivity of the allylboration reaction is controlled via the Alder ene reaction, which generates the E -configured allylboronate subunit predominantly, thereby leading to the syn -allylboration product.
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Sušnik et al. (2014) studied this question.
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