A phosphorus(III)-mediated formal [4+1]-cycloaddition of 1,2-dicarbonyls and o-quinone methides to provide 2,3-dihydrobenzofurans is described. By exploiting the carbene-like nature of dioxyphospholenes, dihydrobenzofurans bearing a quaternary center at C2 are obtained in 30-92% yield with diastereoselectivities up to ≥20:1. This study highlights the subtle steric interactions involved in the [4+1]-cycloannulation and the impact they have on yield and stereoselectivity in dihydrobenzofuran formation.