An operationally simple and concise stereoselective synthesis of both natural 3R, 5 S gingerdiol and 3 S, 5 S gingerdiol has been achieved from achiral n‐heptanal by employing iterative proline catalysed α‐aminoxylation, followed by Horner−Wadsworth−Emmons or Wittig olefination reactions as key steps. The adducts formed in high enantiopurity as well as syn or anti‐1,3‐diols units were synthesized with excellent diastereoselectivity from γ‐hydroxy aldehyde by using D or L‐ proline.