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The first highly asymmetric catalytic synthesis of densely functionalized dihydrobenzofurans is reported, which starts from
ortho
‐hydroxy‐containing
para
‐quinone methides. The reaction relies on an unprecedented formal [4+1]‐annulation of these quinone methides with allenoates in the presence of a commercially available chiral phosphine catalyst. The chiral dihydrobenzofurans were obtained as single diastereomers in yields up to 90 % and with enantiomeric ratios up to 95:5.