Simple, parallel and dynamic: asymmetric hydroboration reactions of racemic intramolecular Diels‐Alder furan (IMDAF) cycloadducts give regiodivergent outcomes in which simple, parallel and dynamic kinetic resolutions of the substrate enantiomers may be observed.

We report parallel kinetic resolution of intramolecular Diels‐Alder cycloadducts, where up to five stereocentres are defined using asymmetric hydroboration as the enantiodiscriminating reaction, and reveal evidence for dynamic kinetic resolution based on a reversible cycloaddition.