An asymmetric [3 + 2] formal cycloaddition reaction between oxindole α-keto esters and enals has been developed. This α,γ-regioselective reaction afforded multifunctional carbocyclic oxindoles via dienamine-enamine cascade reaction followed by isomerization. Furthermore, a highly enantioselective Diels-Alder reaction was demonstrated between 2,4-dienals and oxindole α-keto esters via trienamine intermediates. Chiral secondary amine catalyzed the both reactions under mild conditions and the cyclized products were isolated in moderate to good yields with good diastereoselectivities (>20:1 dr) and enantioselectivities (up to 99 %). © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim