A highly stereoselective method for the synthesis of functionalized 3‐oxabicyclo[3.3.1]nonan‐2‐one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Michael‐hemiacetalization‐Michael reaction of (E)‐3‐aryl‐2‐nitroprop‐2‐enols and (E)‐7‐aryl‐7‐oxohept‐5‐enals followed by a PCC oxidation. Using the modularly designed organocatalysts (MDOs) self‐assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good yields (up to 84%), excellent diastereoselectivities (≥99:1 dr), and high enantioselectivities (up to 96% ee).