AbstractA new highly diastereoselective synthetic route to trans‐2,3‐dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross‐metathesis/isomerization/allylboration sequence starting from 2‐allyl‐substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti‐homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O‐demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.