An enantioselective 1,4-addition of α,β-unsaturated carboxylic acids with cycloalkanones has been developed by using chiral amine-boronic acid cooperative catalysts. In the presence of a chiral amine and boronic acid, cycloalkanones and carboxylic acids are activated as chiral enamines and mixed anhydrides, respectively. The corresponding 1,4-adducts are obtained in high yield with high enantioselectivity. Furthermore, subsequent oxylactonization of the 1,4-adducts gives spirolactones with high diastereoselectivity.

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http://dx.doi.org/10.1002/anie.202007639DOI Listing

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