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Despite the proven value in utilizing pyrone dienes to create molecular complexity via Diels-Alder reactions with varied dienophiles, few examples of effective catalytic, asymmetric variants of this process have been developed. Herein, we show that the use of Jørgensen-Hayashi-type catalysts can convert an array of α,β-unsaturated aldehydes into chiral dienamines that can formally add in a Diels-Alder fashion to a number of electron-deficient pyrones of the coumalate-type to generate optically active [2.2.2]-bicyclic lactones. In most cases, the reactions proceed with good to excellent diastereo- and enantiocontrol (up to 99% ee). Models to explain that stereoselectivity, as well as several additional transformations of the resultant products, are also presented.

Asymmetric pyrone Diels–Alder reactions enabled by dienamine catalysis