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We describe here the design and development of an organocatalytic Prins cyclization. In the presence of a confined chiral imidodiphosphoric acid catalyst, salicylaldehydes react with 3‐methyl‐3‐buten‐1‐ol to afford highly functionalized 4‐methylenetetrahydropyrans in excellent regio‐ and enantioselectivity. The extreme steric demand of the acid catalyst is key for the success of this transformation.